4-Chlorophenyl Isocyanate → HCID 24960674, compound

HRID 2196600Notes

Reaction equation

HRID 2196600 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:22][CH:19]2[CH2:18][CH2:17][N:16]([CH2:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)[CH2:21][CH2:20]2)=[O:32])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 59756883HCID 59756883, compound

Product 1

HCID 24960674HCID 24960674, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-((6,7-Dimethoxyquinolin-4-yl)methyl)piperidin-4-amine (150 mg, 0.50 mmol) was dissolved in DCM (5 mL). While stirring, 4-chlorophenyl isocyanate (84 uL, 0.65 mmol) was added dropwise at rt, and the reaction was allowed to stir for 15 hours. The solvent was removed and the crude compound was columned using 100% DCM to 5% MeOH to give the desired product 1-(4-chlorophenyl)-3-(1-((6,7-dimethoxyquinolin-4-yl)methyl)piperidin-4-yl)urea (50 mg, 0.11 mmol, 22% yield). MS (ESI pos. ion) m/z: 455.2 (MH+). Calc'd exact mass for C24H27ClN4O3: 454.

Workup

  1. stirringto stir for 15 hours
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-c7e6223e41e2498e87f833af5543ff17
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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