Water → 5-Chloro-3-(2,4-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-one

HRID 449800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449800
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[C:11]2([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[O:38][CH3:39])[N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.[N:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][C:48]=2[S:50](Cl)(=[O:52])=[O:51])[CH:43]=[CH:42][CH:41]=1.O>CN(C)C=O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([S:50]([C:48]1[CH:47]=[CH:46][CH:45]=[C:44]3[C:49]=1[N:40]=[CH:41][CH:42]=[CH:43]3)(=[O:51])=[O:52])[C:12](=[O:17])[C:11]2([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1[O:38][CH3:39])[N:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH2:22][CH2:23]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 292208-Quinolinesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 684279685-Chloro-3-(2,4-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1,3-dihydroindol-2-one

Produkt 1

HCID 684279695-Chloro-3-(2,4-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-oneAusbeute 39,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Potassium tert-butoxide (26.6 mg, 0.24 mmol) was added to a solution of 5-chloro-3-(2,4-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1,3-dihydroindol-2-one (0.10 g, 0.22 mmol) in dimethylformamide (4 mL) at 0° C., and the mixture was stirred at 0° C. for 1 hour. Then 8-quinolinesulfonyl chloride (53.9 mg, 0.24 mmol) was added to the reaction solution while cooling in ice, and the mixture was stirred at room temperature for 12 hours. Water was cautiously added to the mixture, which was extracted twice with ethyl acetate. The combined organic phase was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. Chromatographic purification of the residue on silica gel (mobile phase gradient 0-7% methanol in dichloromethane) afforded 57.0 mg of the title compound.

Aufarbeitung

  1. temperaturewhile cooling in ice
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionwas extracted twice with ethyl acetate
  4. washThe combined organic phase was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customChromatographic purification of the residue on silica gel (mobile phase gradient 0-7% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-96a933410c7b4379acc181639bfc0357
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486931B2

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