Dimethylformamide → 4-{2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethylcarbamoyl}-3,3-dimethyl-butanoic acid

HRID 228958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228958
CN(C)C=O.Cl[CH2:7][CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([O:20][C:21]3[C:22]([CH3:31])=[N:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:32][CH3:33].[C:34](=[O:37])([O-])[O-:35].[K+].[K+].[CH3:40][C:41]1([CH3:49])[CH2:46][C:45](=[O:47])[NH:44]C(=O)[CH2:42]1>O>[CH3:33][O:32][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:10]=1[O:9][CH2:8][CH2:7][NH:44][C:45]([CH2:46][C:41]([CH3:49])([CH3:42])[CH2:40][C:34]([OH:35])=[O:37])=[O:47])[N:17]=[CH:16][CH:15]=[C:14]2[O:20][C:21]1[C:22]([CH3:31])=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 142924,4-Dimethylpiperidine-2,6-dioneHCID 230782727-(2-Chloro-ethoxy)-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline2×

Produkt 1

HCID 577563394-{2-[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-ethylcarbamoyl}-3,3-dimethyl-butanoic acidAusbeute 5,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N,N-Dimethylformamide (1 ml) was added to 7-(2-chloro-ethoxy)-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (compound 353) (50 mg), potassium carbonate (53 mg), and 4,4-dimethylpiperidine-2,6-dione (54 mg), and the mixture was stirred at 80° C. overnight and then at 100° C. for one day. The reaction solution was cooled to room temperature, water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (3.5 mg, yield 5%).

Aufarbeitung

  1. waitat 100° C. for one day
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionthe mixture was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b96a6086272b4f5f80f517345f9cbf61
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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