Dimethylformamide → N11-Ethyl-6,11-dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one

HRID 1898873Notes

Reaction equation

[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[H-].[Na+].I[CH2:25][CH3:26]>O>[CH2:25]([N:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[NH:10][C:11](=[O:12])[C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:6]1=2)[CH3:26]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 15 g of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one and 150 ml DMF was heated to 50° C. To the slurry was added 7.5 g (2 equiv) of 50% sodium hydride in mineral oil dispersion, during which time the temperature rose to 65° C. The mixture was cooled to 40° C. and then 6.0 ml of iodoethane was added. The resulting mixture was stirred at room temperature overnight, then poured into 700 ml of water and extracted with 700 ml of ether. The ether phase was dried (MgSO4) and concentrated to dryness. The crude product was purified by column chromatography on basic alumina to yield 3.6 g (21% of theory) of 6,11-dihydro-11-ethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, m.p. 210°-220° C.

Workup

customrose to 65° C
temperatureThe mixture was cooled to 40° C.
extractionextracted with 700 ml of ether
dry with materialThe ether phase was dried (MgSO4)
concentrationconcentrated to dryness
customThe crude product was purified by column chromatography on basic alumina

Sources & evidence

ORD record: ord-3a31c605a8f049f8a7f47472c481bc70
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571809

Reaction notes

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