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

HRID 878314Notes

Reaction equation

HRID 878314 reaction equation
[F: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.[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]([OH:26])=O)(=[O:20])=[O:19]>>[F: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:24](=[O:26])[C:23]2[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=[C:21]([S:18]([CH3:17])(=[O:19])=[O:20])[CH:22]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663178[4-(5-Fluoro-2-methyl-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 70663248N-[4-(5-Fluoro-2-methyl-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from [4-(5-fluoro-2-methyl-phenyl)-pyridin-3-yl]-methyl-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (example 114, intermediate a) after a reaction time of 20.5 hours. The compound was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless foam (20%). MS (ESI): m/z=467.10 [M+H]+.

Workup

  1. customThe compound was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-ac225890efc4415c80b854cf07565956
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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