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

HRID 363333ノート

反応式

HRID 363333 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c0fcbeb6fa764235875a3d60b1dc7306
出典データセット
uspto-grants-1999_02
特許番号
US05874427

反応ノート

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