2-Methoxyethanol → 5-(4-Chloro-phenyl)-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2-methoxy-ethoxy)-nicotinamide

HRID 1766450Notes

Reaction equation

HRID 1766450 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[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]([CH:28]1[CH2:30][CH2:29]1)([OH:27])[CH3:26].[CH3:31][O:32][CH2:33][CH2:34][OH:35]>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:8]2[C:7]([O:35][CH2:34][CH2:33][O:32][CH3:31])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:23][CH2:24][C:25]([CH:28]2[CH2:30][CH2:29]2)([OH:27])[CH3:26])=[O:12])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 742994-Chlorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 211096921-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 119513015-(4-Chloro-phenyl)-N-(2-cyclopropyl-2-hydroxy-propyl)-6-(2-methoxy-ethoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 11, using 5-bromo-6-chloro-nicotinic acid methylester, 2-methoxy-ethanol (commercially available), 4-chlorophenyl-boronic acid (commercially available) and 1-amino-2-cyclopropyl-propan-2-ol (commercially available) as starting materials. MS (m/e): 405.4 (MH+).

Workup

  1. customdescribed for the preparation of Example 11

Sources & evidence

ORD record
ord-8758eb5da9e84cfe9f0d1ad600995f5d
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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