Sodium hydride → HCID 67087741、化合物

HRID 1035847

反応式

HRID 1035847 の反応式
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]3([C:32]4[C:33]([O:38][CH2:39][CH3:40])=[N:34][CH:35]=[CH:36][CH:37]=4)[C:27]4[C:22](=[CH:23][C:24]([F:30])=[C:25]([C:28]#[N:29])[CH:26]=4)[NH:21][C:20]3=[O:31])=[O:17])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1.[CH3:41][O:42][C:43]1[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[CH:45][C:44]=1[S:51](Cl)(=[O:53])=[O:52]>CN(C)C=O>[CH3:3][N:4]1[CH2:5][CH2:6][CH:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]3([C:32]4[C:33]([O:38][CH2:39][CH3:40])=[N:34][CH:35]=[CH:36][CH:37]=4)[C:27]4[C:22](=[CH:23][C:24]([F:30])=[C:25]([C:28]#[N:29])[CH:26]=4)[N:21]([S:51]([C:44]4[CH:45]=[CH:46][C:47]([O:49][CH3:50])=[CH:48][C:43]=4[O:42][CH3:41])(=[O:53])=[O:52])[C:20]3=[O:31])=[O:17])[CH2:12][CH2:11]2)[CH2:8][CH2:9]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 670876865-Cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 67087741HCID 67087741、化合物収率 47%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

9.2 mg (0.19 mmol) of sodium hydride (50% dispersion in mineral oil) were added to a solution of 50 mg (0.10 mmol) of 5-cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate in 2 ml of anhydrous dimethylformamide under a nitrogen atmosphere and while cooling in an ice bath. The mixture was stirred at 0° C. for 10 min and then 29 mg (0.12 mmol) of 2,4-dimethoxyphenylsulfonyl chloride were added, and stirring was continued at room temperature for 30 min. The reaction mixture was poured into ice-water and then extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 20% methanol in dichloromethane). 34 mg of the title compound were obtained as a white solid.

後処理

  1. temperaturewhile cooling in an ice bath
  2. stirringstirring
  3. waitwas continued at room temperature for 30 min
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 20% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-5588ba43144240ec9c56763d624c637f
出典データセット
uspto-grants-2013_10
特許番号
US08546401B2

関連ノート

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