Ammonia → (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

HRID 867526Notes

Reaction equation

HRID 867526 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:18]3C=CN=C3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.N.O>CN(C)C=O>[Br:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:18])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 542882441-[[(S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole

Product 1

HCID 22876620(S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 8.8 g (21.3 mmol) of 1-[[(S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole in 20 ml of N,N-dimethylformamide is treated with 3.6 ml (about 47 mmol) of a 25 percent aqueous ammonia solution and the mixture is stirred at room temperature for 1 hour. The mixture is then poured into 100 ml of water, the product is filtered off under suction after 15 minutes, rinsed with water and dried at 80° in a high vacuum. There is obtained (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide of decomposition point 296°.

Workup

  1. filtrationthe product is filtered off under suction after 15 minutes
  2. washrinsed with water
  3. customdried at 80° in a high vacuum

Sources & evidence

ORD record
ord-d2ad20c2104b45d089045eb0528fb74a
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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