3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → N-(2-Chloro-[3,4']bipyridinyl-3'-yl)-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

HRID 878368Notes

Reaction equation

HRID 878368 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH3:15])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:16][S:17]([C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23]([OH:25])=O)(=[O:19])=[O:18]>>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:15])[C:23](=[O:25])[C:22]2[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=[C:20]([S:17]([CH3:16])(=[O:18])=[O:19])[CH:21]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 866708262-chloro-N-methyl-3,4'-bipyridin-3'-amine

Product 1

HCID 86670825N-(2-Chloro-[3,4']bipyridinyl-3'-yl)-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from 2-chloro-N-methyl-3,4′-bipyridin-3′-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (example 114, intermediate a) after a reaction time of 18 hours. The compound was purified by silica gel chromatography on a 20 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown foam (12%). MS (ESI): m/z=470.055 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-8b38c77a76b14f43be0880e54e1fd473
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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