Sodium ethoxide → 3-[3-(1-Methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propylamino]-N-o-tolyl-propionamide

HRID 69034Notes

Reaction equation

[O-]CC.[Na+].[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[CH:13]2.Cl[CH2:23][CH2:24][C:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[O:26]>C(O)C>[CH3:20][N:16]1[C:17]2[C:12](=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][NH:5][CH2:23][CH2:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[O:26])=[CH:19][CH:18]=2)[CH:13]=[CH:14][C:15]1=[O:21]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium ethoxide (34 mg) was added to an ethanol solution (5 ml) of 6-(3-amino-propoxy)-1-methyl-1H-quinolin-2-one (116 mg) and 3-chloro-N-o-tolyl-propionamide (148 mg). The mixture was stirred at 60° C. for 5 hours. The reaction mixture was condensed under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1). The purified product was condensed under reduced pressure to give the title compound (115 mg) as a white powder.

Workup

customcondensed under reduced pressure
customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1)
customcondensed under reduced pressure

Sources & evidence

ORD record: ord-b1d2b52014f54062b56ffa3ea3208d88
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822453B2

Reaction notes

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