Pyridine → 1-(4-Chloro-phenylcarbamoyl)-5-(3-fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 2217601Notes

Reaction equation

HRID 2217601 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH:9]([C:11](=[O:30])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:15][C:14]=2[F:29])[NH:8][N:7]=1)=[O:5])[CH3:2].N1C=CC=CC=1.[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]=[C:45]=[O:46])=[CH:40][CH:39]=1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH:9]([C:11](=[O:30])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:15][C:14]=2[F:29])[N:8]([C:45](=[O:46])[NH:44][C:41]2[CH:42]=[CH:43][C:38]([Cl:37])=[CH:39][CH:40]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 76934-Chlorophenyl IsocyanateHCID 688053405-(3-Fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 210259681-(4-Chloro-phenylcarbamoyl)-5-(3-fluoro-2'-methanesulfonyl-biphenyl-4-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3-Fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester (1.520 g) in methylene chloride (12 ml) was added pyridine (4 equiv.) and 4-chlorophenyl isocyanate (1.25 equiv.). Stirred at room temperature for 16 hours. Evaporated and recorded crude 1H: 80156×134RM1—revealed expected product and relatively clean. Purified by silica gel chromatography, eluant 10-100% EtOAc in hexane over 25 mins. Collected 1-(4-chloro-phenylcarbamoyl)-5-(3-fluoro-2′-methanesulfonyl-biphenyl-4-ylcarbamoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester (1.480 g).

Workup

  1. customEvaporated
  2. customPurified by silica gel chromatography, eluant 10-100% EtOAc in hexane over 25 mins

Sources & evidence

ORD record
ord-6e03e993f1de4ad985b81e28a3bb4b40
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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