Ethyl bromoacetate → N6-Methyl-N11-((2-oxoethyl)ethoxy)-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one
反応式
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]2[N:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]1=[O:17].[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[CH2:25]([O:24][C:22]([CH2:21][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3](=[O:17])[C:4]2[CH:16]=[CH:15][CH:14]=[N:13][C:5]1=2)=[O:23])[CH3:26]参加物
反応条件
- 温度
- 50 °C
実験手順
To 1.0 g (4.4 mmoles) of 5,6-dihydro-6-methyl-11H-pyrido[2,3-b][1,5]benzodiazepin-5-one in 50 ml of dimethylformamide was added 0.25 g (5 mmol) of 50% sodium hydride in oil. The reaction mixture was then stirred at 50° C. for an additional 2 h and then 0.6 ml (5 mmol) of ethyl bromoacetate was added. The reaction mixture was then stirred at 50° C. for an additional 3 h. It was then cooled to room temperature and the solvent was evaporated. The residue was dissolved in methylene chloride, washed with water, dried over anhydrous sodium sulfate and evaporated to obtain 2.0 g of the crude product. It was further purified by column chromatography (silica gel) using 10% ethyl acetate/methylene chloride as eluent to obtain 250 mg of pure 5,6-dihydro-11-(ethoxy-carbonyl)methyl-6-methyl-11H-pyrido[2,3-b][1,5]benzodiazepin-5-one, m.p. 99°-100° C.
後処理
- stirringThe reaction mixture was then stirred at 50° C. for an additional 3 h
- temperatureIt was then cooled to room temperature
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in methylene chloride
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
- customto obtain 2.0 g of the crude product
- customIt was further purified by column chromatography (silica gel)
出典と根拠
- ORDレコード
- ord-2d979e1ea2084a4a9c545fb9b26bb182
- 出典データセット
- uspto-grants-1996_11
- 特許番号
- US05571809
反応ノート
読み込み中…