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

HRID 1766482Notes

Reaction equation

HRID 1766482 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:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[NH2:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]1[OH:33].[CH3:34][O:35][CH2:36][CH2:37][OH:38]>>[OH:33][C@@H:28]1[CH2:29][CH2:30][CH2:31][CH2:32][C@H:27]1[NH:26][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=2)[C:7]([O:38][CH2:37][CH2:36][O:35][CH3:34])=[N:6][CH:5]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinate

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 23, using 5-bromo-6-chloro-nicotinic acid methyl ester, 2-methoxy-ethanol (commercially available), 4-trifluoromethylphenylboronic acid (commercially available) and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (m/e): 439 (MH+).

Workup

  1. customdescribed for the preparation of Example 23

Sources & evidence

ORD record
ord-197f49c5815e4b6b854d96260b9d7eee
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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