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

HRID 878064Notes

Reaction equation

HRID 878064 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH3:15])[CH:7]=1.[F:17][C:18]([F:33])([F:32])[C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:22](Cl)=[O:23]>CCCCCCC.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:15])[C:22](=[O:23])[C:21]2[CH:20]=[C:19]([C:18]([F:33])([F:32])[F:17])[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 70663391[4-(5-Chloro-2-methyl-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 86670719N-[4-(5-Chloro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-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-(5-chloro-2-methyl-phenyl)-pyridin-3-yl]-methyl-amine and 3,5-bis(trifluoromethyl)benzoyl chloride (CAS RN 1271-19-8) and using a gradient of n-heptane:EtOAc (100:0 to 70:30) for the chromatographic purification. Colorless solid (35%). MS (ESI): m/z=473.084 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-a3aa81d959ef4b5bbd1c84f2b73d6973
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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