3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → [[4-(2-Chloro-phenyl)-pyridin-3-yl]-(3-methanesulfonyl-5-trifluoromethyl-benzoyl)-amino]-acetic acid methyl ester

HRID 878329Notes

Reaction equation

HRID 878329 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18].[CH3:20][S:21]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[C:27](O)=[O:28])(=[O:23])=[O:22]>>[CH3:1][O:2][C:3](=[O:19])[CH2:4][N:5]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:27](=[O:28])[C:26]1[CH:30]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:32]=[C:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH:25]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663245[4-(2-Chloro-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester

Product 1

HCID 70663165[[4-(2-Chloro-phenyl)-pyridin-3-yl]-(3-methanesulfonyl-5-trifluoromethyl-benzoyl)-amino]-acetic acid methyl ester

Procedure

The title compound was prepared in analogy to example 90, from [4-(2-chloro-phenyl)-pyridin-3-ylamino]-acetic acid methyl ester and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (example 114, intermediate a) after a reaction time of 6 hours at room temperature. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (Flashmaster) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light red foam (25%). MS (ESI): m/z=527.066 [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-3ad9e49d473f48e1af3c6bad226abead
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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