3-(Morpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acid → N-[4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl]-N-methyl-3-morpholin-4-ylsulfonyl-5-(trifluoromethyl)benzamide

HRID 878292Notes

Reaction equation

HRID 878292 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:5]([N:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[O:22][CH3:23])[CH3:8])=[O:6].[N:31]1([S:37](C2C=C(C=C(C(F)(F)F)C=2)C(O)=O)(=[O:39])=[O:38])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:7]([CH3:8])[C:5](=[O:6])[C:4]2[CH:24]=[C:25]([C:27]([F:28])([F:30])[F:29])[CH:26]=[C:2]([S:37]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)(=[O:39])=[O:38])[CH:3]=2)=[C:16]([O:22][CH3:23])[CH:17]=1

Participants

3

Reactant 2

HCID 179642763-(Morpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acidHCID 70663278HCID 70663278, compound

Product 1

HCID 60196904N-[4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl]-N-methyl-3-morpholin-4-ylsulfonyl-5-(trifluoromethyl)benzamide

Procedure

The title compound was prepared in analogy to example 90, from 4-(4-fluoro-2-methoxyphenyl)-N-methylpyridin-3-amine (example 129, intermediate) and 3-(morpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acid after a reaction time of 64 hours. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (ISCO) system eluting with EtOAc (isocratic). Light yellow solid (34%). MS (ESI): m/z=554.14 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with EtOAc (isocratic)

Sources & evidence

ORD record
ord-d6d420ed5e3d4ea68dcd4fc7a583979f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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