4-Chlorophenylboronic acid → HCID 11952021, compound

HRID 1766479Notes

Reaction equation

HRID 1766479 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[CH3:12][C:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.Cl.[NH2:29][CH2:30][C@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[OH:37]>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:7]([O:17][CH2:16][C:13]3([CH3:12])[CH2:15][CH2:14]3)=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:29][CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]2[OH:37])=[O:11])=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 137701(1-Methylcyclopropyl)methanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 53393211HCID 53393211, compound

Product 1

HCID 11952021HCID 11952021, compound

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, 1-methyl-cyclopropanemethanol, (4-chloro-phenyl)-boronic acid and cis-2-aminomethyl-1-cyclohexanol hydrochloride as starting materials to yield racemic 5-(4-chloro-phenyl)-N-((1RS,2RS)-2-hydroxy-cyclohexylmethyl)-6-(1-methyl-cyclopropylmethoxy)-nicotinamide. MS (ISP) 429.5 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 75

Sources & evidence

ORD record
ord-17957ffe29c048d6abada33e31480a4b
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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