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

HRID 69021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69021
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a59254b7466b4827825ca80037de7c22
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822453B2

Notizen zur Reaktion

Wird geladen…