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

HRID 1766477Notes

Reaction equation

HRID 1766477 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[CH:12]1([CH2:16][OH:17])[CH2:15][CH2:14][CH2:13]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.Cl.[NH2:29][C@@H:30]1[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]1[OH:36]>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:7]([O:17][CH2:16][CH:12]3[CH2:15][CH2:14][CH2:13]3)=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:29][C@@H:30]2[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]2[OH:36])=[O:11])=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 78130CyclobutylcarbinolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 119520195-(4-chloro-phenyl)-6-cyclobutylmethoxy-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, cyclobutanemethanol, (4-chloro-phenyl)-boronic acid and (1R,2R)-2-amino-cyclohexanol hydrochloride as starting materials to yield 5-(4-chloro-phenyl)-6-cyclobutylmethoxy-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide. MS (ISP) 415.4 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-3818748c2522436c98ba7f7171dca600
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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