Dimethylformamide → {N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)amino}acetic acid ethyl ester

HRID 69022Notes

Reaction equation

HRID 69022 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].CN(C=O)C.[CH3:19][N:20]1[C:29]2[C:24](=[CH:25][C:26]([O:30][CH2:31][CH2:32][CH2:33][NH:34][CH2:35][C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]1=[O:42]>C(OCC)(=O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][N:34]([CH2:33][CH2:32][CH2:31][O:30][C:26]1[CH:25]=[C:24]2[C:29](=[CH:28][CH:27]=1)[N:20]([CH3:19])[C:21](=[O:42])[CH:22]=[CH:23]2)[CH2:35][C:36]1[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=1)[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 86762689HCID 86762689, compound

Product 1

HCID 86762688{N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)amino}acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (1.66 g) and ethyl bromoacetate (1.16 ml) were added to a DMF solution (50 ml) of 1-methyl-6-{3-[(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-one (1.5 g), and stirred at room temperature overnight. The reaction mixture was added to ice water, and extraction with ethyl acetate was performed. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0→85:15). The purified product was condensed under reduced pressure to give the title compound (1.28 g) as a orange oil.

Workup

  1. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0→85:15)
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-798610e6436e48a0950e457675f84c73
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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