3-Dimethylsulfamoyl-5-trifluoromethyl-benzoic acid → N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-dimethylsulfamoyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

HRID 878146Notes

Reaction equation

HRID 878146 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[C:4]([O:21][CH3:22])[CH:3]=1.[CH3:23][N:24]([CH3:41])[S:25]([C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[C:31](O)=[O:32])(=[O:27])=[O:26]>>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH2:16][C:17]([F:18])([F:19])[F:20])[C:31](=[O:32])[C:30]2[CH:34]=[C:35]([C:37]([F:39])([F:38])[F:40])[CH:36]=[C:28]([S:25](=[O:26])(=[O:27])[N:24]([CH3:41])[CH3:23])[CH:29]=2)=[C:4]([O:21][CH3:22])[CH:3]=1

Participants

3

Reactant 2

HCID 179640083-Dimethylsulfamoyl-5-trifluoromethyl-benzoic acidHCID 70663602[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 60197918N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-dimethylsulfamoyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from [4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine (example 132, intermediate a) and 3-dimethylsulfamoyl-5-trifluoromethyl-benzoic acid (Buttpark Ltd.). The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of CH2Cl2: EtOAc (100:0 to 90:10), followed by preparative HPLC using a gradient of methanol:water (10:50 to 95:5). Light brown foam (13%). MS (ESI): m/z=598.104 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of CH2Cl2: EtOAc (100:0 to 90:10)

Sources & evidence

ORD record
ord-d841edc9875845b7b1c2ee1977612f26
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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