Ethyl bromoacetate → N6-Methyl-N11-((2-oxoethyl)ethoxy)-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one

HRID 1898876

Reaction equation

[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]

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-2d979e1ea2084a4a9c545fb9b26bb182
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571809

Linked notes

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