Sodium hydride → N6-Methyl-N11-((2-oxoethyl)t-butoxy)-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one

HRID 1898875

반응식

HRID 1898875 반응식
[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][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CN(C)C=O>[C: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])([CH3:28])([CH3:27])[CH3:26]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 4532455H-Pyrido(2,3-b)(1,5)benzodiazepin-5-one, 6,11-dihydro-6-methyl-

생성물 1

HCID 453259N6-Methyl-N11-((2-oxoethyl)t-butoxy)-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one수율 43.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To 0.8 g (3.5 mmoles) of 5,6-dihydro-6-methyl-11H-pyrido[2,3-b][1,5]benzodiazepin-5-one in 75 ml of dimethylformamide was added 0.2 g (4.0 mmol) of 50% sodium hydride in oil, and the reaction mixture was stirred at 60° C. for 2 h. It was then cooled to room temperature and 0.78 g (4.0 mmoles) of t-butyl bromoacetate was added dropwise, and the reaction mixture was allowed to stir overnight. Excess sodium hydride was carefully quenched with water and the solvent was evaporated. The residue was dissolved in methylene chloride, washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 2.0 g of crude product. Purification by column chromatography (silica gel) using 10% ethyl acetate/methylene chloride afforded 0.52 g of pure 5,6-Dihydro-11-(t-butoxycarbonyl)methyl-6-methyl-11H-pyrido[2,3-b][1,5]benzodiazepin-5-one, m.p. 64°-65° C.

후처리

  1. temperatureIt was then cooled to room temperature
  2. stirringto stir overnight
  3. customExcess sodium hydride was carefully quenched with water
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customEvaporation of the solvent
  9. customgave 2.0 g of crude product
  10. customPurification by column chromatography (silica gel)

출처 및 근거

ORD 기록
ord-61bf9511f07446c0b87352f62f64c2a0
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05571809

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