4-Cyanobenzoyl chloride → N-[(3RS,4SR)-4-(4-chloro-phenyl)-1-(4-cyano-benzoyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide

HRID 1951090Notes

Reaction equation

HRID 1951090 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][NH:11][CH2:10][CH:9]2[N:13]([CH3:28])[C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[CH:4][CH:3]=1.[C:29]([C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)#[N:30]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][N:11]([C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:31]([C:29]#[N:30])=[CH:32][CH:33]=3)[CH2:10][CH:9]2[N:13]([CH3:28])[C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 67025659N-[(3RS,4SR)-4-(4-Chloro-phenyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide

Product 1

HCID 67025651N-[(3RS,4SR)-4-(4-chloro-phenyl)-1-(4-cyano-benzoyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide

Procedure

In analogy to the procedure described for the synthesis of example 88, the title compound N-[(3RS,4SR)-4-(4-chloro-phenyl)-1-(4-cyano-benzoyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide was prepared from N-[(3RS,4SR)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide using 4-cyanobenzoyl chloride instead of 4-fluorobenzoyl chloride and was obtained as a light brown oil. MS m/e: 542.1 [M+H]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 88
  2. customwas obtained as a light brown oil

Sources & evidence

ORD record
ord-7d845afbb99a43eea456f9fafafb6d30
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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