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

HRID 1898875

Reaktionsgleichung

Reaktionsgleichung von HRID 1898875
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 453259N6-Methyl-N11-((2-oxoethyl)t-butoxy)-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-oneAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-61bf9511f07446c0b87352f62f64c2a0
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05571809

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