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 1504194Notes

Reaction equation

HRID 1504194 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

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 33143863-chloro-N-methyl-N-phenylpropanamideHCID 86762689HCID 86762689, compound

Product 1

HCID 86762690N-methyl-3-{N'-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N'-(pyridin-4-ylmethyl)amino}-N-phenylpropionamideYield 2.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. 1H-NMR (CDCl3) δ ppm: 1.80-1.98 (2H, m), 2.26 (2H, t, J=7.3 Hz), 2.53 (2H, t, J=6.5 Hz), 2.81 (2H, t, J=7.3 Hz), 3.24 (3H, s), 3.44 (2H, s), 3.72 (3H, s), 3.98 (2H, t, J=6.0 Hz), 6.73 (1H, d, J=9.5 Hz), 6.93 (1H, d, J=2.7 Hz), 7.00-7.19 (5H, m), 7.24-7.41 (4H, m), 7.60 (1H, d, J=9.5 Hz), 8.42 (2H, d, J=5.4 Hz).

Workup

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

Sources & evidence

ORD record
ord-92db649ef9334b26b54463b9c6468f74
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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