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

HRID 69021Notes

Reaction equation

HRID 69021 reaction equation
[C:1](=[O:4])([O-:3])[O-].[K+].[K+].CN(C=O)C.[CH3:12][N:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]1=[O:35].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>C(OCC)(=O)C>[CH2:41]([O:40][C:38](=[O:39])[CH2:37][O:3][C:1](=[O:4])[N:27]([CH2:26][CH2:25][CH2:24][O:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:13]([CH3:12])[C:14](=[O:35])[CH:15]=[CH:16]2)[CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH3:42]

Participants

6

Reactant 4

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

Product 1

HCID 90369233{N-[3-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-4-ylmethyl)carbamoyloxy}acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Potassium carbonate (1.66 g) was added to a DMF solution (50 ml) of 1-methyl-6-{3-[(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-one (1.5 g). The mixture was cooled to 0° C., and ethyl bromoacetate (1.16 ml) was added to the mixture 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=20:1→10:1). The purified product was condensed under reduced pressure. The residue was recrystallized from ether, and dried to give the title compound (0.55 g) as a white powder.

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=20:1→10:1)
  5. customcondensed under reduced pressure
  6. customThe residue was recrystallized from ether
  7. customdried

Sources & evidence

ORD record
ord-a59254b7466b4827825ca80037de7c22
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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