Water → 1-(5-Methoxy-2-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}phenyl)-1-ethanone

HRID 228650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228650
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([O:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[C:25](=[O:27])[CH3:26])=[CH:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:28][CH3:29].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:10]2[C:9]3[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[C:7]([O:28][CH3:29])[CH:8]=3)[N:13]=[CH:12][CH:11]=2)=[C:18]([C:25](=[O:27])[CH3:26])[CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 577563951-(2-{[7-(3-Chloropropoxy)-6-methoxy-4-quinolyl]oxy}-5-methoxyphenyl)-1-ethanone2×

Produkt 1

HCID 230784641-(5-Methoxy-2-{[6-methoxy-7-(3-morpholinopropoxy)-4-quinolyl]oxy}phenyl)-1-ethanoneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-(2-{[7-(3-Chloropropoxy)-6-methoxy-4-quinolyl]oxy}-5-methoxyphenyl)-1-ethanone (compound 121) (100 mg), morpholine (63 mg), and potassium carbonate (166 mg) were suspended in N,N-dimethylformamide (2 ml), and the suspension was stirred at 80° C. overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using methanol-chloroform to give the title compound (55 mg, yield 49%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water and saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-67f249b418f14239b1543b63e9e0e972
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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