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

HRID 449800ノート

反応式

HRID 449800 の反応式
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

参加物

6

反応物 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

生成物 1

HCID 684279695-Chloro-3-(2,4-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-one収率 39.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-96a933410c7b4379acc181639bfc0357
出典データセット
uspto-grants-2013_07
特許番号
US08486931B2

反応ノート

読み込み中…