3-Dimethylsulfamoyl-5-trifluoromethyl-benzoic acid → 3-Dimethylsulfamoyl-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

HRID 878132Notes

Reaction equation

HRID 878132 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[CH3:16][N:17]([CH3:34])[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]>>[CH3:34][N:17]([CH3:16])[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]([N:2]([CH3:1])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:26])(=[O:19])=[O:20]

Participants

3

Reactant 2

HCID 179640083-Dimethylsulfamoyl-5-trifluoromethyl-benzoic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 706634853-Dimethylsulfamoyl-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 3-[(dimethylamino)sulfonyl]-5-(trifluoromethyl)benzoic acid (Butt Park Ltd.). The product was purified a second time using preparative HPLC (Phenomenex Gemini® column) and a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2). Light brown foam (20%). MS (ESI): m/z=478.1 [M+H]+.

Workup

  1. customThe product was purified a second time

Sources & evidence

ORD record
ord-34cc86f7b1b24387be13f95ddb933beb
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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