ethyl 5-(2,4-dimethoxybenzyl)-8-fluoro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate → N-Desmethylflumazenil

HRID 1447338Notes

Reaction equation

HRID 1447338 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:10]=2[N:9]2[CH:19]=[N:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:8]2[CH2:7]1>FC(F)(F)C(O)=O>[F:18][C:15]1[CH:16]=[CH:17][C:10]2[N:9]3[CH:19]=[N:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:8]3[CH2:7][NH:6][C:12](=[O:13])[C:11]=2[CH:14]=1

Participants

3

Reactant 1

HCID 20515335ethyl 5-(2,4-dimethoxybenzyl)-8-fluoro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

Product 1

HCID 6426758N-Desmethylflumazenil

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

13.0 g (29.6 mmol) of ethyl 5-(2,4-dimethoxybenzyl)-8-fluoro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate are heated to boiling under reflux for 4 hours in 45 ml of trifluoroacetic acid. After evaporation of the dark red suspension in vacuo, the residue is treated with water and made alkaline with ca 100 ml of 15 percent potassium carbonate solution. The separated material is filtered off under suction and washed with water. After recrystallisation from ca 500 ml of ethanol, there is obtained ethyl 8-fluoro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 298° C.

Workup

  1. customAfter evaporation of the dark red suspension in vacuo
  2. additionthe residue is treated with water
  3. filtrationThe separated material is filtered off under suction
  4. washwashed with water
  5. customAfter recrystallisation from ca 500 ml of ethanol

Sources & evidence

ORD record
ord-72d75b5152914c58a5d489f3e1321b51
Source dataset
uspto-grants-1982_02
Patent number
US04316839

Reaction notes

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