2-Methoxyethanol → 5-(4-chloro-phenyl)-N-(3-hydroxy-2,2-dimethyl-propyl)-6-(2-methoxy-ethoxy)-nicotinamide

HRID 1766469Notes

Reaction equation

HRID 1766469 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7]([OH:11])=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[NH2:23][CH2:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27].[CH3:30][O:31][CH2:32][CH2:33]O>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:8]2[C:7]([O:11][CH2:33][CH2:32][O:31][CH3:30])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:23][CH2:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27])=[O:12])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 742994-Chlorophenylboronic acidHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 2764315Methyl 5-bromo-6-hydroxynicotinate

Product 1

HCID 119518345-(4-chloro-phenyl)-N-(3-hydroxy-2,2-dimethyl-propyl)-6-(2-methoxy-ethoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 102, using 5-bromo-6-hydroxy-nicotinic acid methyl ester, 2-methoxyethanol, (4-chloro-phenyl)-boronic acid and 3-amino-2,2-dimethyl-1-propanol as starting materials to yield 5-(4-chloro-phenyl)-N-(3-hydroxy-2,2-dimethyl-propyl)-6-(2-methoxy-ethoxy)-nicotinamide. MS (ISP) 393.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-ab657b8ef1554d618c31ca78ef15a1eb
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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