3-Fluoro-5-(trifluoromethyl)benzoyl chloride → N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-fluoro-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

HRID 878138Notes

Reaction equation

HRID 878138 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[C:4]([O:21][CH3:22])[CH:3]=1.[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:27](Cl)=[O:28]>CCCCCCC.CCOC(C)=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH2:16][C:17]([F:18])([F:19])[F:20])[C:27](=[O:28])[C:26]2[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=[C:24]([F:23])[CH:25]=2)=[C:4]([O:21][CH3:22])[CH:3]=1

Participants

4

Reactant 2

HCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 70663602[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 86670752N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-fluoro-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, intermediate, from [4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine and 3-fluoro-5-(trifluoromethyl)benzoic acid chloride (CAS RN 171243-30-4) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Light yellow foam (39%). MS (ESI): m/z=509.091 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-8be2d20b3e964e90a8fb843fccde7c37
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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