Flumazenil → HCID 20434833, compound

HRID 1154463Notes

Reaction equation

HRID 1154463 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.[C-:23]#N.[K+]>C(O)C#C>[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][C:19]#[CH:23])=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 3373FlumazenilHCID 9032Potassium Cyanide

Product 1

HCID 20434833HCID 20434833, compound

Reagents, catalysts & solvents 1

HCID 7859Propargyl alcoholSolvent

Procedure

A mixture of 20.0 g (65.9 mmol) of ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 1.0 g (15.4 mmol) of potassium cyanide and 100 ml of propargyl alcohol is stirred at 125° for 20 hours and at 135° for 1 hour, evaporated to dryness in vacuo and the residue is taken up in chloroform. The chloroform solution is washed twice with water, dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel while eluting with ethyl acetate. By recrystallization of the resulting material from chloroform/toluene there is obtained 2-propynyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 220°-222°.

Workup

  1. customevaporated to dryness in vacuo
  2. washThe chloroform solution is washed twice with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue is chromatographed on silica gel
  6. washwhile eluting with ethyl acetate
  7. customBy recrystallization of the resulting material from chloroform/toluene there

Sources & evidence

ORD record
ord-fe2dc287e7ea48f8ab4156960e0e093c
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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