(1R,2R)-2-Aminocyclohexanol → N-((trans)-2-Hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1159244Notes

Reaction equation

HRID 1159244 reaction equation
Br[C:2]1[C:3]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[NH2:29][C@@H:30]1[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]1[OH:36]>>[OH:36][C@@H:31]1[CH2:32][CH2:33][CH2:34][CH2:35][C@H:30]1[NH:29][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)[C:3]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 735777(1R,2R)-2-AminocyclohexanolHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 211097055-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid

Product 1

HCID 11951478N-((trans)-2-Hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 31b to c, using 5-bromo-6-(2-methoxy-ethoxy)-nicotinic acid, 4-trifluoromethylphenyl-boronic acid (commercially available) and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 439.0 (M+H+).

Workup

  1. customdescribed for the preparation of Example 31b to c

Sources & evidence

ORD record
ord-dce1c0389f5641fbaf73f719f3d527d3
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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