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

HRID 1159224Notes

Reaction equation

HRID 1159224 reaction equation
CO[C:3]([C:5]1[CH:10]=[C:9](Br)[C:8](=[O:12])[NH:7][CH:6]=1)=[O:4].[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]O>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:9]2[C:8]([O:12][CH2:34][CH2:33][O:32][CH3:31])=[N:7][CH:6]=[C:5]([CH:10]=2)[C:3]([NH:23][CH2:24][C:25]([CH:28]2[CH2:30][CH2:29]2)([OH:27])[CH3:26])=[O:4])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 742994-Chlorophenylboronic acidHCID 2764315Methyl 5-bromo-6-hydroxynicotinateHCID 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 6, using 5-bromo-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester, 2-methoxy-ethanol (commercially available), 4-chlorophenyl-boronic acid (commercially available) and rac-1-amino-2-cyclopropyl-propan-2-ol (commercially available) as starting materials. MS (ISP): 405.4 (MH+).

Workup

  1. customdescribed for the preparation of Example 6

Sources & evidence

ORD record
ord-77271cad95a04612beca5827df8c1196
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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