2-Methoxyethanol → N-((trans)-2-Hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

HRID 1159245Notes

Reaction equation

HRID 1159245 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.[NH2:27][C@@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]1[OH:34].[CH3:35][O:36][CH2:37][CH2:38][OH:39]>>[OH:34][C@@H:29]1[CH2:30][CH2:31][CH2:32][CH2:33][C@H:28]1[NH:27][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:19]2[CH:20]=[CH:21][C:16]([O:15][C:14]([F:26])([F:25])[F:13])=[CH:17][CH:18]=2)[C:7]([O:39][CH2:38][CH2:37][O:36][CH3:35])=[N:6][CH:5]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 11951479N-((trans)-2-Hydroxy-cyclohexyl)-6-(2-methoxy-ethoxy)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, 2-methoxy-ethanol (commercially available), 4-trifluoromethoxyphenyl-boronic acid (commercially available) and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 455.1 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-b5fd00a351924d1fa40a16283b01ab93
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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