Figure4_dataset.pbtxt

description: "Partial Information from figure 4 of paper.\302\240"
reactions {
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            units: MICROMOLE
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            units: MICROMOLE
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        identifiers {
          type: SMILES
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            units: MICROMOLE
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        identifiers {
          type: SMILES
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          volume {
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            units: MICROLITER
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        units: MICROLITER
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    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
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            units: MICROLITER
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        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
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          volume {
            value: 5.0
            units: MICROLITER
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        identifiers {
          type: NAME
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          type: SMILES
          details: "NAME resolved by the PubChem API"
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          moles {
            value: 0.05
            units: MICROMOLE
          }
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      }
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  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
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      volume {
        value: 25.0
        units: MICROLITER
      }
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  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
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        }
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          volume {
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            units: MICROLITER
          }
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      units: HOUR
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        analysis_key: "UPLC-MS"
        type: YIELD
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        type: LCMS
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    }
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    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
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  inputs {
    key: "Amine"
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      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
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          moles {
            value: 3.75
            units: MICROMOLE
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        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
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            value: 7.5
            units: MICROMOLE
          }
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      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
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            units: MICROMOLE
          }
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            units: MICROLITER
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            units: MICROMOLE
          }
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          type: SMILES
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            units: MICROMOLE
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        identifiers {
          type: SMILES
          value: "CS(=O)C"
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            units: MICROLITER
          }
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        units: MICROLITER
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          type: SMILES
          details: "NAME resolved by the PubChem API"
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          type: SMILES
          details: "NAME resolved by the PubChem API"
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        units: MICROLITER
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    type: ADDITION
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          type: SMILES
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            units: MICROLITER
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    }
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      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
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}
reactions {
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      components {
        identifiers {
          type: SMILES
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        }
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            value: 3.75
            units: MICROMOLE
          }
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      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
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          type: SMILES
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            units: MICROMOLE
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            units: MICROMOLE
          }
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        identifiers {
          type: SMILES
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            units: MICROMOLE
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            units: MICROLITER
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      components {
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          type: SMILES
          details: "NAME resolved by the PubChem API"
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            units: MICROLITER
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          details: "NAME resolved by the PubChem API"
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        units: MICROLITER
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          type: SMILES
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            units: MICROLITER
          }
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        is_normalized: true
        uses_authentic_standard: false
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        }
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        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
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      email: "spencer_dreher@merck.com"
    }
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    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
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}
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        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
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            value: 3.75
            units: MICROMOLE
          }
        }
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      }
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          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
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            value: 7.5
            units: MICROMOLE
          }
        }
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          type: SMILES
          value: "[Cu]I"
        }
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            value: 0.25
            units: MICROMOLE
          }
        }
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      }
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            units: MICROLITER
          }
          volume_includes_solutes: true
        }
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      }
      addition_order: 2
    }
  }
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    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
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        }
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            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
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          type: SMILES
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            units: MICROMOLE
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          type: SMILES
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            units: MICROLITER
          }
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      material {
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        units: MICROLITER
      }
    }
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      details: "Nitrogen Filled"
    }
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      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
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            units: MICROLITER
          }
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      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 24.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 1.38
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 41.08
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 54.2
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 28.908
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 39.96
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 78.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cccc(c1NC(=O)C(=O)O)C"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 1.63
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 30.8
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 78.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 33.6
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 2.53
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 50.56
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 16.26
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 32.472
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 6.66
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 81.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COc1cccc(c1NC(=O)C(=O)O)OC"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 22.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 49.28
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 52.8
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 1.15
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 66.36
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 43.36
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 19.8
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 59.94
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 78.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)F)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 39.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 52.36
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 7.8
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 38.4
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 60.04
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 27.1
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 8.316
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 6.66
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 80.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(c(c1)S(=O)(=O)N2CCCCC2)NC(=O)C(=O)O)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)CC1CCc2cc(cc3c2n1c(=O)c(=O)[nH]3)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 2.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)c1c2n(cn1)-c3ccc(cc3C(=O)N(C2)C)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 40.04
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)Br)c3ccc(cc3)S(=O)(=O)C)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC1(C(=C(C(=O)O1)Oc2ccc(cn2)N3CCCCC3)c4ccc(cc4)S(=O)(=O)C)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 15.6
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)Br)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)OC(=O)N2Cc3c(ccc(c3C2)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 28.8
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1ccc(cc1)COC(=O)N2CCC[C@@H]2C(=O)c3c[nH]c4c3cc(cc4)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)Br)Cl)CC1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCOC(=O)N1CCC(=C2c3ccc(cc3CCc4c2ncc(c4)N5CCCCC5)Cl)CC1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 47.4
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(ccc1Cn2c3c(cc(cc3Br)F)c4c2[C@H](CC4)CC(=O)O)Cl"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(ccc1Cn2c3c(cc(cc3N4CCCCC4)F)c5c2[C@H](CC5)CC(=O)O)Cl"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "COC(=O)[C@@H]1C[C@H](CN1C(=O)OCc2ccccc2)OC(=O)N3Cc4cccc(c4C3)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 54.2
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1F)OC2CCN(CC2)c3cc(on3)c4nnn(n4)CC(=O)O)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(c(c(nc2Br)C(=O)NCc3ccc(cc3)F)O)nc1"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(c(c(nc2N3CCCCC3)C(=O)NCc4ccc(cc4)F)O)nc1"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)Br)C)C#N"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc(cc(c1Oc2c(c(nc(n2)Nc3ccc(cc3)C#N)N)N4CCCCC4)C)C#N"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)Br)OC)N[C@@H]4CCC[C@H]4O)n(c1=O)CCO"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCn1c(=O)c2c(nc(n2Cc3ccc(c(c3)N4CCCCC4)OC)N[C@@H]5CCC[C@H]5O)n(c1=O)CCO"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)Br"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "C[C@]1(CC(=O)N(/C(=N\\C(=O)OC(C)(C)C)/N1)C)c2cc(cs2)N3CCCCC3"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc(c(cc1N2C[C@@H](OC2=O)Cn3ccnn3)F)N4CCCCC4"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 6.66
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)I"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CCCc1nc2ccc(cc2c(=O)n1Cc3ccc(cc3)c4ccccc4S(=O)(=O)NC(C)(C)C)N5CCCCC5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 61.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "Cc1cc2c(cc1Cl)C3(CCN(CC3)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "Cc1cc2c(cc1N3CCCCC3)C4(CCN(CC4)C(=O)OC(C)(C)C)C[C@H]2C(C)(C)NC(=O)C"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1cc2c(cc1Cl)[C@@](OC(=O)N2)(C#CC3CC3)C(F)(F)F"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "c1cc2c(cc1N3CCCCC3)C(OC(=O)N2)(C#CC4CC4)C(F)(F)F"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}
reactions {
  inputs {
    key: "Amine"
    value {
      components {
        identifiers {
          type: SMILES
          value: "C1CCNCC1"
        }
        amount {
          moles {
            value: 3.75
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: false
      }
      components {
        identifiers {
          type: SMILES
          value: "[O-]P(=O)([O-])[O-].[K+].[K+].[K+]"
        }
        amount {
          moles {
            value: 7.5
            units: MICROMOLE
          }
        }
        reaction_role: REAGENT
      }
      components {
        identifiers {
          type: SMILES
          value: "[Cu]I"
        }
        amount {
          moles {
            value: 0.25
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
          volume_includes_solutes: true
        }
        reaction_role: SOLVENT
      }
      addition_order: 2
    }
  }
  inputs {
    key: "Aryl Halide"
    value {
      components {
        identifiers {
          type: SMILES
          value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)Cl)OCc4ccc5ccccc5n4"
        }
        amount {
          moles {
            value: 2.5
            units: MICROMOLE
          }
        }
        reaction_role: REACTANT
        is_limiting: true
      }
      addition_order: 1
    }
  }
  inputs {
    key: "Catalyst"
    value {
      components {
        identifiers {
          type: SMILES
          value: "c1c(cc(cc1C(F)(F)F)NC(=O)C(=O)O)C(F)(F)F"
        }
        amount {
          moles {
            value: 0.5
            units: MICROMOLE
          }
        }
        reaction_role: CATALYST
      }
      components {
        identifiers {
          type: SMILES
          value: "CS(=O)C"
        }
        amount {
          volume {
            value: 12.5
            units: MICROLITER
          }
        }
        reaction_role: SOLVENT
      }
      addition_order: 3
    }
  }
  setup {
    vessel {
      type: WELL_PLATE
      details: "96 Glass Vials"
      material {
        type: GLASS
      }
      volume {
        value: 250.0
        units: MICROLITER
      }
    }
    environment {
      type: GLOVE_BOX
      details: "Nitrogen Filled"
    }
  }
  conditions {
    temperature {
      control {
        type: DRY_ALUMINUM_PLATE
      }
      setpoint {
        value: 80.0
        units: CELSIUS
      }
    }
    stirring {
      type: STIR_BAR
      details: "Magnetic Stir Bar"
    }
  }
  workups {
    type: ADDITION
    details: "The reaction vials were then cooled to r.t.\nand diluted with 100 \316\274L of 5% AcOH in DMSO, containing 1,3,5-trimethoxybenzene (0.005M) and were\nshaken vigorously."
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CS(C)=O"
        }
        amount {
          volume {
            value: 95.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC(=O)O"
        }
        amount {
          volume {
            value: 5.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
      components {
        identifiers {
          type: NAME
          value: "1,3,5-trimethoxybenzene"
        }
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "COc1cc(OC)cc(OC)c1"
        }
        amount {
          moles {
            value: 0.05
            units: MICROMOLE
          }
        }
        reaction_role: INTERNAL_STANDARD
      }
    }
  }
  workups {
    type: ALIQUOT
    details: "25 microliter of resulting solution is taken"
    amount {
      volume {
        value: 25.0
        units: MICROLITER
      }
    }
  }
  workups {
    type: ADDITION
    details: "To the 25 microliter aliquot 700 microliter of MeCN was added prior to UPLC-MS Analysis"
    input {
      components {
        identifiers {
          type: SMILES
          details: "NAME resolved by the PubChem API"
          value: "CC#N"
        }
        amount {
          volume {
            value: 700.0
            units: MICROLITER
          }
        }
        reaction_role: WORKUP
      }
    }
  }
  outcomes {
    reaction_time {
      value: 18.0
      units: HOUR
    }
    products {
      identifiers {
        type: SMILES
        value: "CC(C)(C)Sc1c2cc(ccc2n(c1CC(C)(C)C(=O)OC)Cc3ccc(cc3)N4CCCCC4)OCc5ccc6ccccc6n5"
      }
      is_desired_product: true
      measurements {
        analysis_key: "UPLC-MS"
        type: YIELD
        uses_internal_standard: true
        is_normalized: true
        uses_authentic_standard: false
        percentage {
          value: 0.0
        }
      }
      reaction_role: PRODUCT
    }
    analyses {
      key: "UPLC-MS"
      value {
        type: LCMS
        details: "Quantitative analysis was accomplished by reverse phase UPLC (Waters\nX-BridgeTM BEH 2.5 micron, RP C-18, 2.1 x 50 mm column, eluents: MeCN-H2O containing 0.05%\nTFA) using an internal standard (either 4,4-di-tert-butyl biphenyl, or 1,3,5-trimethoxybenzene as noted\nin the experiment)"
        instrument_manufacturer: "Waters"
      }
    }
  }
  provenance {
    experimenter {
      name: "Spencer Dreher"
      orcid: "0000-0002-5094-1218"
      organization: "Merck"
      email: "spencer_dreher@merck.com"
    }
    city: "Rahway, NJ"
    doi: "10.1039/C5SC04751J"
    publication_url: "https://pubs.rsc.org/en/content/articlelanding/2016/SC/C5SC04751J#!divAbstract"
    record_created {
      time {
        value: "6/2/2021, 8:10:58 AM"
      }
      person {
        name: "Michael Wleklinski"
        orcid: "0000-0001-6735-4696"
        organization: "Merck"
        email: "michael.wleklinski@merck.com"
      }
    }
  }
  reaction_id: "ord-cea65357d8b94f30a162d3c6cc495457"
}