HCID 13987114, compound → 7-chloro-3-(3-heptyl-1,2,4-oxadiazol-5-yl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 867563Notes

Reaction equation

HRID 867563 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:18]3C=C[N:20]=[CH:19]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][N:20]=[C:19]([CH2:8][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 13987114HCID 13987114, compound

Product 1

HCID 212899697-chloro-3-(3-heptyl-1,2,4-oxadiazol-5-yl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.80 g (20 mmol) of 1-[[7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl]carbonyl]imidazole, 50 ml of N,N-dimethylformamide and 3.2 g (20 mmol) of heptanecarboxamidoxime are stirred at 100° overnight. The solution is then evaporated and the residue is dissolved in methylene chloride. The organic solution is washed with water and the solvent is evaporated. By chromatography of the residue on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate there is obtained 7-chloro-3-(3-heptyl-1,2,4-oxadiazol-5-yl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 108°-110°.

Workup

  1. customThe solution is then evaporated
  2. dissolutionthe residue is dissolved in methylene chloride
  3. washThe organic solution is washed with water
  4. customthe solvent is evaporated
  5. washBy chromatography of the residue on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-fbc39952379040f0b36ad1e1f65c513e
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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