Dimethylformamide → 6-(2-Methoxyethylcarbonyl)-7-methoxy-4-(1-ethylcarbamoyl-indol-5-yloxy)quinoline

HRID 853502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853502
[H-].[Na+].[CH3:3][N:4]([CH3:7])[CH:5]=[O:6].COCCN[C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)NC=C2)=[O:14].C1(OC(=O)[NH:45][CH2:46][CH3:47])C=CC=CC=1.[C:49]([O:52][CH2:53][CH3:54])(=O)C>O>[CH3:49][O:52][CH2:53][CH2:54][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:36]=[C:35]2[C:7](=[CH:30][CH:29]=1)[N:4]([C:5](=[O:6])[NH:45][CH2:46][CH3:47])[CH:3]=[CH:34]2)=[O:14]

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2802346phenyl N-ethylcarbamateHCID 229365306-(2-Methoxyethylcarbamoyl)-7-methoxy-4-(indol-5-yloxy) quinoline

Produkt 1

HCID 229370126-(2-Methoxyethylcarbonyl)-7-methoxy-4-(1-ethylcarbamoyl-indol-5-yloxy)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

After adding 60% sodium hydride (10 mg) to dimethylformamide (1 ml), the mixture was stirred at room temperature, 6-(2-methoxyethylcarbamoyl)-7-methoxy-4-(indol-5-yloxy) quinoline (10 mg) was added, and the mixture was stirred for another 15 minutes. Ethylcarbamic acid phenyl ester (43 mg) was then added and the mixture was stirred for 1 hour. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Ethyl acetate was used for recrystallization to obtain the title compound (27 mg).

Aufarbeitung

  1. stirringthe mixture was stirred for another 15 minutes
  2. stirringthe mixture was stirred for 1 hour
  3. washthe organic layer was washed with water and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customEthyl acetate was used for recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-b1affab448ad43f49db9b59d835358f4
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253286B2

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