[(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone → HCID 178485739, compound

HRID 1951105Notes

Reaction equation

HRID 1951105 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([NH:14][CH3:15])[CH2:12][N:11]([C:16]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([C:26]4([CH3:29])[CH2:28][CH2:27]4)=[O:25])[CH2:20][CH2:19]3)=[O:17])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:30][C@@H:31]1[CH2:36][CH2:35][C@H:34]([C:37]([OH:39])=O)[CH2:33][CH2:32]1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][N:11]([C:16]([CH:18]3[CH2:19][CH2:20][N:21]([C:24]([C:26]4([CH3:29])[CH2:27][CH2:28]4)=[O:25])[CH2:22][CH2:23]3)=[O:17])[CH2:12][CH:13]2[N:14]([CH3:15])[C:37]([C@H:34]2[CH2:33][CH2:32][C@@H:31]([OH:30])[CH2:36][CH2:35]2)=[O:39])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 67025815[(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanoneHCID 178525779HCID 178525779, compound

Product 1

HCID 178485739HCID 178485739, compound

Procedure

In analogy to the procedure described for the synthesis of example 97, the title compound cis-4-hydroxy-cyclohexanecarboxylic acid {(3RS,4SR)-4-(3,4-dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-amide was prepared from {4-[(3SR,4RS)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-piperidin-1-yl}-(1-methyl-cyclopropyl)-methanone using cis-4-hydroxycyclohexanecarboxylic acid instead of 4-chloro-3-(trifluoromethyl)benzoic acid and was obtained as a light brown oil. MS m/e: 564.4 [M]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 97
  2. customwas obtained as a light brown oil

Sources & evidence

ORD record
ord-5ee199e025b84c0b89e58d9933215175
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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