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

HRID 878070Notes

Reaction equation

HRID 878070 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][CH2:15][C:16]([F:19])([F:18])[F:17].[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:25](Cl)=[O:26]>CCCCCCC.CCOC(C)=O>[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]([CH2:15][C:16]([F:19])([F:17])[F:18])[C:25](=[O:26])[C:24]1[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=[C:22]([C:21]([F:20])([F:35])[F:36])[CH:23]=1

Participants

4

Reactant 2

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 70663252[4-(2-Chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 60196999N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-N-(2,2,2-trifluoro-ethyl)-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, intermediate, from [4-(2-chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine and 3,5-bis(trifluoromethyl)benzoyl chloride (CAS RN 1271-19-8) and using a gradient of n-heptane:EtOAc (100:0 to 40:60) for the chromatographic purification. Light yellow solid (138 mg, 63%). MS (ESI): m/z=527.057 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-a7af42d510024424940cec2cccae3f38
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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