4-Fluorophenylboronic acid → 6-(cyclopropylmethyl-methyl-amino)-5-(4-fluoro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

HRID 1929866Notes

Reaction equation

HRID 1929866 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.Cl.[CH:14]1([CH2:17][NH:18][CH3:19])[CH2:16][CH2:15]1.[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.[NH2:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[OH:37]>>[CH:14]1([CH2:17][N:18]([CH3:19])[C:7]2[C:8]([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)=[CH:9][C:4]([C:3]([NH:30][C@@H:31]3[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]3[OH:37])=[O:12])=[CH:5][N:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 2856454-Fluorophenylboronic acidHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 12919210(Cyclopropylmethyl)(methyl)amine hydrochloride

Product 1

HCID 119498916-(cyclopropylmethyl-methyl-amino)-5-(4-fluoro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-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, cyclopropylmethyl methylamine hydrochloride (commercially available), 4-fluorophenyl-boronic acid (commercially available) and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 398.3 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-36984173ef594ac39c850e987a28e9fd
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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