Triethylamine → 5,11-Dihydro-11-[[(2-propynyl)-amino]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 4168

Reaction equation

[CH2:1]([NH2:4])[C:2]#[CH:3].Cl[C:6]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[NH:11][C:10]2[CH:20]=[CH:21][CH:22]=[N:23][C:9]1=2)=[O:7].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([NH:4][C:6]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[NH:11][C:10]2[CH:20]=[CH:21][CH:22]=[N:23][C:9]1=2)=[O:7])[C:2]#[CH:3]

Participants

Conditions

Temperature: 40 °C

Procedure

5.5 g (0.1 mol) of propargylamine were added dropwise with stirring at ambient temperature to a suspension of 27.3 g (0.1 mol) of 11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 10.0 g (0.1 mol) of triethylamine in 500 ml of chloroform, whereupon the temperature rises to 35° C. The mixture is stirred for a further 30 minutes at 40° C., then filtered over activated charcoal and the reaction solution is evaporated to dryness in vacuo. After the oily residue has been decocted with ethyl acetate the desired product is obtained in the form of a colourless crystalline mass in a yield of 20.7 g (71% of theory).

Workup

customrises to 35° C
filtrationfiltered over activated charcoal
customthe reaction solution is evaporated to dryness in vacuo
customis obtained in the form of a colourless crystalline mass in a yield of 20.7 g (71% of theory)

Sources & evidence

ORD record: ord-da6aacba240a48b7804ec076824d5006
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04724236

Linked notes

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