4-Chloro-3-(trifluoromethyl)benzoic acid → HCID 75047549, compound

HRID 1951146Notes

Reaction equation

HRID 1951146 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([C:11]([N:13]3[CH2:17][CH:16]([NH:18][CH3:19])[CH:15]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=4)[CH2:14]3)=[O:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][C:30]=1[C:38]([F:41])([F:40])[F:39]>>[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([N:18]([CH:16]2[CH:15]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:14][N:13]([C:11]([CH:8]3[CH2:9][CH2:10][N:5]([CH2:4][CH:1]4[CH2:3][CH2:2]4)[CH2:6][CH2:7]3)=[O:12])[CH2:17]2)[CH3:19])=[O:35])=[CH:31][C:30]=1[C:38]([F:41])([F:40])[F:39]

Participants

3

Reactant 2

HCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 67025771(1-cyclopropylmethyl-piperidin-4-yl)-[(3SR,4RS)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-methanone

Product 1

HCID 75047549HCID 75047549, compound

Procedure

In analogy to the procedure described for the synthesis of example 87 (step c), the title compound 4-chloro-N-[(3RS,4SR)-1-(1-cyclopropylmethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-N-methyl-3-trifluoromethyl-benzamide was prepared from (1-cyclopropylmethyl-piperidin-4-yl)-[(3SR,4RS)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-methanone instead of N-[(3RS,4SR)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-4-methoxy-N-methyl-3-trifluoromethyl-benzamide using 4-chloro-3-(trifluoromethyl)benzoic acid instead of 1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid and was obtained as a white foam. MS m/e: 616.3 [M]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 87 (step c)
  2. customwas obtained as a white foam

Sources & evidence

ORD record
ord-7944cfd1641c4a0fb64c9a2e117e701e
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

Loading…