(4-Methanesulfonamidophenyl)boronic acid → N-((1R,2R)-2-hydroxy-cyclohexyl)-5-(4-methanesulfonylamino-phenyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

HRID 598254Notes

Reaction equation

HRID 598254 reaction equation
Br[C:2]1[C:3]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[N:4][C:5]([C:18]([F:21])([F:20])[F:19])=[C:6]([CH:17]=1)[C:7]([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16])=[O:8].[CH3:28][S:29]([NH:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)(=[O:31])=[O:30]>>[OH:16][C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]1[NH:9][C:7](=[O:8])[C:6]1[CH:17]=[C:2]([C:36]2[CH:35]=[CH:34][C:33]([NH:32][S:29]([CH3:28])(=[O:30])=[O:31])=[CH:38][CH:37]=2)[C:3]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[N:4][C:5]=1[C:18]([F:21])([F:20])[F:19]

Participants

3

Reactant 2

HCID 2773537(4-Methanesulfonamidophenyl)boronic acidHCID 866348015-Bromo-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

Product 1

HCID 44240774N-((1R,2R)-2-hydroxy-cyclohexyl)-5-(4-methanesulfonylamino-phenyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 1d, using 5-bromo-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-2-trifluoromethyl-nicotinamide and 4-methanesulfonylaminophenylboronic acid as starting materials, MS (ISP) 556.1 (M+H)+.

Sources & evidence

ORD record
ord-b28583bbcb494517adf06517efcebf8e
Source dataset
uspto-grants-2011_03
Patent number
US07897621B2

Reaction notes

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