Sodium ethoxide → N-methyl-3-{N'-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N'-(pyridin-4-ylmethyl)amino}-N-phenylpropionamide

HRID 69023Notes

Reaction equation

[O-]CC.[Na+].Cl[CH2:6][CH2:7][C:8]([N:10]([CH3:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[CH3:18][N:19]1[C:28]2[C:23](=[CH:24][C:25]([O:29][CH2:30][CH2:31][CH2:32][NH:33][CH2:34][C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]1=[O:41]>C(O)C>[CH3:17][N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8](=[O:9])[CH2:7][CH2:6][N:33]([CH2:32][CH2:31][CH2:30][O:29][C:25]1[CH:24]=[C:23]2[C:28](=[CH:27][CH:26]=1)[N:19]([CH3:18])[C:20](=[O:41])[CH:21]=[CH:22]2)[CH2:34][C:35]1[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium ethoxide (34 mg) and 3-chloro-N-methyl-N-phenylpropionamide (148 mg) were added to a ethanol solution (5 ml) of 1-methyl-6-{3-[(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-one (161 mg), and stirred at 60° C. for 8.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound (5.6 mg) as a colorless oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1)
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-27acb1dc8180429880573ace2e0b8502
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822453B2

Reaction notes

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