Water → (S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

HRID 223339Notes

Reaction equation

HRID 223339 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([OH:18])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:12]3[CH:11]=[CH:15][N:14]=[CH:13]3)=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 22828765(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid

Product 1

HCID 54332091(S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.54 g (30 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid and 6.32 g (39 mmol) of N,N'-carbonyldiimidazole in 50 ml of dry dimethylformamide are stirred at room temperature for 1 hour and at 50° for 1 hour. Subsequently, the mixture is poured into about 300 ml of water, the precipitated material is filtered off under suction, washed with water and dried to constant weight. There is obtained (S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole of melting point 240°-241.5°.

Workup

  1. filtrationthe precipitated material is filtered off under suction
  2. washwashed with water
  3. customdried to constant weight

Sources & evidence

ORD record
ord-83e485bb88ea4d8da80e2677657f719e
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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