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

HRID 1766513Notes

Reaction equation

HRID 1766513 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.Cl.[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38]>>[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:31][C@@H:32]2[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]2[OH:38])=[O:12])=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 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 Example 74, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethyl methylamine hydrochloride, (4-chloro-phenyl)-boronic acid and (1R,2R)-2-amino-cyclohexanol hydrochloride as starting materials to yield 5-(4-chloro-phenyl)-6-(cyclopropylmethyl-methyl-amino)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide. MS (ISP) 414.3 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 74

Sources & evidence

ORD record
ord-0089722ce3454e8480351daece0489c8
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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