Sodium hydride → 3-{Bis[4-(methoxymethoxy)phenyl]methyl}-2-[4-(2-chlorophenyl)piperazinylsulfonyl]-1-(2-dimethylaminoethyl)-indole

HRID 442866ノート

反応式

HRID 442866 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH2:44][O:45][CH3:46])=[CH:39][CH:38]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[S:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:7][CH:6]=1.[H-].[Na+].Cl.[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53]Cl.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:37]2[CH:38]=[CH:39][C:40]([O:43][CH2:44][O:45][CH3:46])=[CH:41][CH:42]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:53][CH2:52][N:51]([CH3:55])[CH3:50])[C:13]=2[S:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[CH2:26][CH2:25]2)(=[O:22])=[O:23])=[CH:7][CH:6]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 676918923-(Bis[4-(methoxymethoxy)phenyl]methyl)-2-[4-(2-chlorophenyl)piperazinylsulfonyl]indole

生成物 1

HCID 867540463-{Bis[4-(methoxymethoxy)phenyl]methyl}-2-[4-(2-chlorophenyl)piperazinylsulfonyl]-1-(2-dimethylaminoethyl)-indole収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of Compound 241 (1.2 g, 1.81 mmol) obtained in Example 242 in 25 ml of N,N-dimethylformamide was portionwise added sodium hydride (60% in oil, 160 mg, 3.81 mmol) with stirring at 0° C., and 2-dimethylaminoethylchloride hydrochloride (260 mg, 1.81 mmol) was added thereto, followed by heating to 80° C. and then stirring for 7 hours. A saturated aqueous solution of ammonium chloride was added to the reaction solution for neutralization, and water was added thereto followed by extraction with ethyl acetate. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was purified with silica gel column chromatography (ethyl acetate/hexane=2/1) to give 1.1 g (yield: 85%) of the title compound.

後処理

  1. temperatureby heating to 80° C.
  2. stirringstirring for 7 hours
  3. additionwas added
  4. extractionthereto followed by extraction with ethyl acetate
  5. washThe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto give a crude product
  9. customThe obtained crude product
  10. customwas purified with silica gel column chromatography (ethyl acetate/hexane=2/1)

出典と根拠

ORDレコード
ord-1a5d966484844594ae3bb69b186abd34
出典データセット
uspto-grants-1999_04
特許番号
US05891902

反応ノート

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