4-Chlorophenyl Isocyanate → HCID 11526142, compound

HRID 602332Notes

Reaction equation

HRID 602332 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=1.[Cl-].[CH3:19][O:20][C:21]1([O:42][CH3:43])[CH2:25][NH2+:24][C@@H:23]([C:26](=[O:41])[NH:27][C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]3=[O:40])=[CH:30][CH:29]=2)[CH2:22]1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:24]2[CH2:25][C:21]([O:42][CH3:43])([O:20][CH3:19])[CH2:22][C@@H:23]2[C:26]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]3=[O:40])=[CH:30][CH:29]=2)=[O:41])=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 86607078HCID 86607078, compound

Product 1

HCID 11526142HCID 11526142, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.4 0.12 ml of triethylamine and 127 mg (0.830 mmol) of 4-chlorophenyl isocyanate are added to a solution of 250 mg (0.658 mmol) of (R)-4,4-dimethoxy-2-[4-(2-oxo-2H-pyridin-1-yl)phenylcarbamoyl]pyrrolidinium chloride in 10 ml of dichloromethane. After stirring at room temperature for one hour, the reaction mixture is evaporated, and the residue is chromatographed on a silica-gel column with dichloromethane/methanol 95:5 as eluent, giving 1-N-[(4-chlorophenyl)]-2-N-{[4-(2-oxo-2H-pyridin-1-yl)phenyl]}-(R)-4,4-dimethoxypyrrolidine-1,2-dicarboxamide (“A7”) as a colourless solid; ESI 497.

Workup

  1. customthe reaction mixture is evaporated
  2. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol 95:5 as eluent

Sources & evidence

ORD record
ord-2b3132821f3c4aa1ab947a971b31ab26
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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