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

HRID 878140Notes

Reaction equation

HRID 878140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[C:4]([O:20][CH3:21])[CH:3]=1.[CH3:22][N:23]([CH3:40])[S:24]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:30](O)=[O:31])(=[O:26])=[O:25]>C(Cl)Cl.CCOC(C)=O>[CH3:22][N:23]([CH3:40])[S:24]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:38])([F:37])[F:39])[CH:35]=1)[C:30]([N:14]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[O:20][CH3:21])[CH2:15][C:16]([F:18])([F:17])[F:19])=[O:31])(=[O:25])=[O:26]

Participants

4

Reactant 2

HCID 179640083-Dimethylsulfamoyl-5-trifluoromethyl-benzoic acidHCID 70663530[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 866707533-Dimethylsulfamoyl-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared in analogy to example 90, from [4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine and 3-dimethylsulfamoyl-5-trifluoromethyl-benzoic acid (Buttpark Ltd.) and using a gradient of CH2Cl2: EtOAc (100:0 to 90:10) for the chromatographic purification. Light yellow foam (42%). MS (ESI): m/z=580.112 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-33a09f6c87404b87b5abc1e57e43e24b
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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