Reaktionsgleichung
[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]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
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.
Aufarbeitung
- 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)
Quellen und Nachweise
- ORD-Eintrag
- ord-2d979e1ea2084a4a9c545fb9b26bb182
- Quelldatensatz
- uspto-grants-1996_11
- Patentnummer
- US05571809
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