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

HRID 878328Notes

Reaction equation

HRID 878328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH:14][CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18].[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:28](O)=[O:29])(=[O:24])=[O:23]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH2:15][CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:28](=[O:29])[C:27]1[CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=[C:25]([S:22]([CH3:21])(=[O:24])=[O:23])[CH:26]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663437[4-(2-Chloro-phenyl)-pyridin-3-yl]-(2-methanesulfonyl-ethyl)-amine

Product 1

HCID 70663260N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2-methanesulfonyl-ethyl)-5-trifluoromethyl-benzamideYield 13%

Procedure

The title compound was prepared in analogy to example 90, from [4-(2-chloro-phenyl)-pyridin-3-yl]-(2-methanesulfonyl-ethyl)-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)-benzoic acid (example 114, intermediate a) after a reaction time of 18 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). A further purification step using preparative HPLC (Gemini NX) with a gradient of MeOH:water (containing 0.05% formic acid) (80:20 to 98:2) gave the desired compound as a colorless oil (13%). MS (ESI): m/z=561.052 [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)
  3. customA further purification step

Sources & evidence

ORD record
ord-74c4c3f7c2f540fc8a85614c367b500f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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