Water → 3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

HRID 1606952Notes

Reaction equation

HRID 1606952 reaction equation
Cl/[CH:2]=[CH:3]\[C:4]1[N:5]=[CH:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[N:10]([CH3:19])[CH2:9][C:8]=12.N12CCCN=C1CCCCC2.O>CN(C)C=O>[C:3]([C:4]1[N:5]=[CH:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[N:10]([CH3:19])[CH2:9][C:8]=12)#[CH:2]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867433543-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515493-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.20 g (8 mmol) of 3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at 145° for 6 hours together with 1.43 ml (9.6 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 30 ml of N,N-dimethylformamide. The reaction mixture was subsequently poured into water and extracted five times with methylene chloride. The organic extracts were washed five times with water, dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate there was obtained 3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one of melting point 191°-193°.

Workup

  1. extractionextracted five times with methylene chloride
  2. washThe organic extracts were washed five times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. washAfter chromatography of the residue on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-27c95111841847cc9b82fb4f5ccd2467
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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