Water → 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606954

Reaction equation

HRID 1606954 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][N:9]([CH3:20])[CH2:10][C:11]3[N:12]([C:13](=O)[NH:14][C:15]=3/[CH:16]=[CH:17]\Cl)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[OH2:32]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:32])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[CH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867433567-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine--one

Product 1

HCID 198515337-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20.2 g (65.5 mmol) of 7-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine--one was heated to boiling under reflux for 5 hours together with 11.7 ml (78.5 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 200 ml of N,N-dimethylformamide. The reaction mixture was subsequently poured into 800 ml of water and extracted four time with methylene chloride. The organic extracts were washed four times with water, dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel while eluting with ethyl acetate and two successive crystallizations from acetonitrile and from ethyl acetate there was obtained 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 201°-202°.

Workup

  1. extractionextracted four time with methylene chloride
  2. washThe organic extracts were washed four 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 two successive crystallizations from acetonitrile and from ethyl acetate

Sources & evidence

ORD record
ord-cbbe1afd9e4849a7a994b5b2448f4990
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Linked notes

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