Cyclopropanemethanol → 6-Cyclopropylmethoxy-N-((trans)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

HRID 1766522Notes

Reaction equation

HRID 1766522 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[OH:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.[F:17][C:18]([F:30])([F:29])[O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.Cl.[NH2:32][C@@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]1[OH:39]>>[CH:14]1([CH2:13][O:12][C:7]2[C:2]([C:23]3[CH:24]=[CH:25][C:20]([O:19][C:18]([F:30])([F:29])[F:17])=[CH:21][CH:22]=3)=[CH:3][C:4]([C:9]([NH:32][C@@H:33]3[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]3[OH:39])=[O:11])=[CH:5][N:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 119516576-Cyclopropylmethoxy-N-((trans)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethyl-cyclopropan, 4-(trifluoromethoxy)-phenylboronic acid and (1R,2R)-2-amino-cyclohexanol hydrochloride as starting materials to yield 6-cyclopropylmethoxy-N-((1R,2R)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide. MS (ISP) 451.1 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 75

Sources & evidence

ORD record
ord-ecded711ef8d4a608cf85ddb00346dc5
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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