3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → N-[4-(5-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-5-trifluoromethyl-benzamide

HRID 878338Notes

Reaction equation

HRID 878338 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH2:14])[CH:7]=1.[CH3:17][S:18]([C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:24](O)=[O:25])(=[O:20])=[O:19]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][C:24](=[O:25])[C:23]2[CH:27]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:29]=[C:21]([S:18]([CH3:17])(=[O:20])=[O:19])[CH:22]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 706633734-(5-Fluoro-2-methoxyphenyl)pyridin-3-amine

Product 1

HCID 70663253N-[4-(5-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from 4-(5-fluoro-2-methoxy-phenyl)-pyridin-3-ylamine and 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (example 114, intermediate a) after a reaction time of 18 hours. The residue was purified by column chromatography eluting with a gradient of n-hexane:EtOAc (40:60 to 20:80. Brown liquid (68%). MS (ESI): m/z=469.2 [M+H]+.

Workup

  1. customThe residue was purified by column chromatography
  2. washeluting with a gradient of n-hexane:EtOAc (40:60 to 20:80

Sources & evidence

ORD record
ord-9751a23ddba946eca176b4946b78c347
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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