Triethylamine → N-(methanesulfonyl)-3-(octahydroindolizin-7-yl)-5-amino-1H-indole

HRID 363333노트

반응식

HRID 363333 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]1[CH:14]2[N:9]([CH2:10][CH2:11][CH:12]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=4)[NH:17][CH:16]=3)[CH2:13]2)[CH2:8][CH2:7]1.C(N(CC)CC)C.[OH-].[NH4+]>CN(C)C=O.CO.C(Cl)Cl.O>[CH3:1][S:2]([N:17]1[C:18]2[C:23](=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[C:15]([CH:12]2[CH2:13][CH:14]3[N:9]([CH2:8][CH2:7][CH2:6]3)[CH2:10][CH2:11]2)=[CH:16]1)(=[O:4])=[O:3]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 31297Methanesulfonyl chlorideHCID 153897613-(Octahydroindolizin-7-yl)-5-amino-1H-indole

생성물 1

HCID 67570698N-(methanesulfonyl)-3-(octahydroindolizin-7-yl)-5-amino-1H-indole수율 50.4%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

The methanesulfonyl chloride (215 mg, 1.87 mmol) was added dropwise to a solution of the 3-(octahydroindolizin-7-yl)-5-amino-1H-indole (320 mg, 1.25 mmol) and triethylamine (0.5 ml) in 10 ml of dimethylformamide. The reaction was stirred at room temperature for 2.5 hours. The reaction was diluted with methanol and concentrated to give a dark semi-solid. This material was dissolved in a mixture of methylene chloride and water, made basic with an ammonium hydroxide solution, then extracted with methylene chloride. The extract was dried over sodium sulfate and concentrated to give a reddish brown oil. The material was purified on a flash column using silica gel (20% methanol in methylene chloride (ammonium hydroxide) as eluent) to give 210 mg of product. (49.7%).

후처리

  1. concentrationconcentrated
  2. customto give a dark semi-solid
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a reddish brown oil
  7. customThe material was purified on a flash column

출처 및 근거

ORD 기록
ord-c0fcbeb6fa764235875a3d60b1dc7306
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874427

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