Water → {2-[(7-{3-[(2-Hydroxyethyl)amino]propoxy}-6-methoxy-4-quinolyl)oxy]-5-methylphenyl}(phenyl)methanone

HRID 228660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228660
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]([CH3:23])=[CH:19][C:18]=3[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:32][CH3:33].[C:34](=[O:37])([O-])[O-].[K+].[K+].O.[CH3:41][N:42](C)C=O>>[OH:37][CH2:34][CH2:41][NH:42][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]([CH3:23])=[CH:19][C:18]=3[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:25])=[CH:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:32][CH3:33]

Komponenten

5

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 57756383(2-{[7-(3-Chloropropoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone2×

Produkt 1

HCID 57756337{2-[(7-{3-[(2-Hydroxyethyl)amino]propoxy}-6-methoxy-4-quinolyl)oxy]-5-methylphenyl}(phenyl)methanoneAusbeute 54 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(2-{[7-(3-Chloropropoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone (compound 132) (68 mg), 4-aminoethanol (25 mg), and potassium carbonate (95 mg) were suspended in N,N-dimethylformamide (3 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 (36 mg, yield 54%).

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-2e56b58b329847e484e0d81b2a7f18c3
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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