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

HRID 1766495Notes

Reaction equation

HRID 1766495 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[CH:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38]>>[CH:13]1([CH2:16][O:17][C:7]2[C:8]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:21][CH:22]=3)=[CH:9][C:4]([C:3]([NH:31][C@@H:32]3[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]3[OH:38])=[O:12])=[CH:5][N:6]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 119516566-Cyclopropylmethoxy-N-((trans)-2-hydroxy-cyclohexyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 11, using 5-bromo-6-chloro-nicotinic acid methylester, cyclopropylmethanol (commercially available), 4-trifluoromethylphenyl-boronic acid (commercially available) and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (m/e): 435 (MH+).

Workup

  1. customdescribed for the preparation of Example 11

Sources & evidence

ORD record
ord-f18c85c623bb4495a22b9965684ea7c7
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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