3,5-Bis(trifluoromethyl)benzoyl chloride → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-cyclopropyl-3,5-bis-trifluoromethyl-benzamide

HRID 878125Notes

Reaction equation

HRID 878125 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH:14][CH:15]1[CH2:17][CH2:16]1.[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23](Cl)=[O:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH:15]1[CH2:17][CH2:16]1)[C:23](=[O:24])[C:22]1[CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=[C:20]([C:19]([F:18])([F:33])[F:34])[CH:21]=1

Participants

3

Reactant 2

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 70663285[4-(2-Chloro-phenyl)-pyridin-3-yl]-cyclopropyl-amine

Product 1

HCID 86670746N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-cyclopropyl-3,5-bis-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 72, intermediate, from [4-(2-chloro-phenyl)-pyridin-3-yl]-cyclopropyl-amine and 3,5-bis(trifluoromethyl)benzoyl chloride (CAS RN 1271-19-8). The compound was purified by two subsequent silica gel chromatographies using a MPLC system (10 g column, gradient of n-heptane:EtOAc (100:0 to 50:50) and n-heptane:EtOAc (100:0 to 60:40)) and by preparative HPLC (phenomenex gemini column) with a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2). Colorless solid (24%). MS (ESI): m/z=485.08 [M+H]+.

Workup

  1. customThe compound was purified by two subsequent silica gel chromatographies

Sources & evidence

ORD record
ord-54c8543d7274443581ed03980a798ba8
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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