4-Chlorophenylboronic acid → HCID 11950413, compound

HRID 1766539Notes

Reaction equation

HRID 1766539 reaction equation
CO[C:3]([C:5]1[CH:6]=[N:7][C:8](Cl)=[C:9](Br)[CH:10]=1)=[O:4].[CH3:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH2:19][OH:20].[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.[NH2:31][CH2:32][C@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]1[OH:39]>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:9]2[C:8]([O:20][CH2:19][C:15]3[N:14]([CH3:13])[CH:18]=[CH:17][N:16]=3)=[N:7][CH:6]=[C:5]([CH:10]=2)[C:3]([NH:31][CH2:32][C@@H:33]2[CH2:38][CH2:37][CH2:36][CH2:35][C@@H:34]2[OH:39])=[O:4])=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 573612(1-methyl-1H-imidazol-2-yl)methanolHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 12483365cis-2-Aminomethyl-1-cyclohexanol

Product 1

HCID 11950413HCID 11950413, compound

Procedure

The title compound was synthesized in analogy to Example 102, using 5-bromo-6-chloro-3-pyridinecarboxylic acid methyl ester, 1-methyl-1H-imidazole-2-methanol, (4-chloro-phenyl)-boronic acid and cis-2-aminomethyl-1-cyclohexanol as starting materials to yield racemic cis-5-(4-chloro-phenyl)-N-(2-hydroxy-cyclohexylmethyl)-6-(1-methyl-1H-imidazol-2-ylmethoxy)-nicotinamide, MS (ISP) 455.3 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 102

Sources & evidence

ORD record
ord-609ee36344164f09b1ca9fb1f163614e
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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