Flumazenil → HCID 20434818, compound

HRID 1154490Notes

Reaction equation

HRID 1154490 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1.O[CH2:24][CH:25]1CC1>CCO.CCO.CCO.CCO.[Ti].[F-].[K+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][CH2:18][CH:19]4[CH2:25][CH2:24]4)=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1

Participants

5

Reactant 2

HCID 3373FlumazenilHCID 75644Cyclopropanemethanol

Product 1

HCID 20434818HCID 20434818, compound

Reagents, catalysts & solvents 2

HCID 2724286Titanium(IV)ethoxideCatalystHCID 522689Potassium FluorideSolvent

Procedure

A mixture of 5 g (16.5 mmol) of ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 1.8 g (8 mmol) of tetraethyl orthotitanate and 16.5 g (230 mmol) of hydroxymethyl-cyclopropane is stirred at 110° overnight, evaporated to dryness, the residue is taken up in methylene chloride and the solution obtained is stirred for 0.5 hour with 50 ml of a saturated potassium fluoride solution. The emulsion obtained is filtered through siliceous earth, the separated organic phase is washed with water, dried over magnesium sulphate and evaporated. By crystallization from ethyl acetate there is obtained cyclopropylmethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 156-157°.

Workup

  1. customevaporated to dryness
  2. customthe solution obtained
  3. customThe emulsion obtained
  4. filtrationis filtered through siliceous earth
  5. washthe separated organic phase is washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customBy crystallization from ethyl acetate

Sources & evidence

ORD record
ord-668efbf55c8b4a9d99a36944498bb161
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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