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

HRID 1159261Notes

Reaction equation

HRID 1159261 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.[Cl: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]>>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:8]2[C:7]([N:18]([CH2:17][CH:14]3[CH2:16][CH2:15]3)[CH3:19])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:30][C@@H:31]2[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]2[OH:37])=[O:12])=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 735777(1R,2R)-2-AminocyclohexanolHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 12919210(Cyclopropylmethyl)(methyl)amine hydrochloride

Product 1

HCID 119498895-(4-chloro-phenyl)-6-(cyclopropylmethyl-methyl-amino)-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-chlorophenyl-boronic acid (commercially available) and (1R,2R)-2-amino-cyclohexanol (commercially available) as starting materials. MS (ISP): 414.3 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-a30e3924ed3240e9aa8fc782aa0aaa0e
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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