Cyclopropanesulfonyl chloride → N-[(3RS,4SR)-1-(1-Cyclopropanesulfonyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([C:14]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH2:11][CH:10]2[N:22]([CH3:37])[C:23](=[O:36])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:38]1([S:41](Cl)(=[O:43])=[O:42])[CH2:40][CH2:39]1>>[CH:38]1([S:41]([N:19]2[CH2:20][CH2:21][CH:16]([C:14]([N:12]3[CH2:13][CH:9]([C:4]4[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=4)[CH:10]([N:22]([CH3:37])[C:23](=[O:36])[C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([C:32]([F:33])([F:34])[F:35])[CH:25]=4)[CH2:11]3)=[O:15])[CH2:17][CH2:18]2)(=[O:43])=[O:42])[CH2:40][CH2:39]1Participants
3
Reactant 2
Product 1
Procedure
In analogy to the procedure described for the synthesis of example 140, the title compound N-[(3RS,4SR)-1-(1-Cyclopropanesulfonyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide was prepared from N-[(3RS,4SR)-4-(3,4-dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide using cyclopropanesulfonylchloride instead of ethanesulfonyl chloride and was obtained as a off-white foam. MS m/e: 662.2 [M]+.
Workup
- customIn analogy to the procedure described for the synthesis of example 140
- customwas obtained as a off-white foam
Sources & evidence
- ORD record
- ord-42b3c07707874f578965018ec527f678
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404679B2
Reaction notes
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