Water → [5-Methyl-2-({6-methoxy-7-[4-(4-tetrahydro-1-pyrrolylpiperidino)butoxy]-4-quinolyl}oxy)phenyl](phenyl)methanone

HRID 228671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228671
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([O:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:33][CH3:34].[N:35]1([CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:11]2[C:10]3[C:15](=[CH:16][C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:43]4[CH2:44][CH2:45][CH:40]([N:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)[CH2:41][CH2:42]4)=[C:8]([O:33][CH3:34])[CH:9]=3)[N:14]=[CH:13][CH:12]=2)=[C:19]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])[CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 787034-(1-Pyrrolidinyl)piperidineHCID 57756358(2-{[7-(4-Chlorobutoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone

Produkt 1

HCID 57756547[5-Methyl-2-({6-methoxy-7-[4-(4-tetrahydro-1-pyrrolylpiperidino)butoxy]-4-quinolyl}oxy)phenyl](phenyl)methanoneAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(2-{[7-(4-Chlorobutoxy)-6-methoxy-4-quinolyl]oxy}-5-methylphenyl)(phenyl)methanone (60 mg), 4-(1-pyrrolidinyl)piperidine (60 mg), and potassium carbonate (90 mg) was 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 (69 mg, yield 90%).

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-beb35cce986e4ed58a898d89bdb716ed
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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