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

HRID 4168
Notes
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Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 239041PropargylamineHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 201529205,11-Dihydro-11-[[(2-propynyl)-amino]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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

  1. customrises to 35° C
  2. filtrationfiltered over activated charcoal
  3. customthe reaction solution is evaporated to dryness in vacuo
  4. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes