N-Hydroxyacetamidine → HCID 14590409, compound

HRID 867553Notes

Reaction equation

HRID 867553 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([N:19]3[CH:23]=[CH:22]N=C3)=[O:18])=[C:4]2[CH2:3]1.C(=NO)([NH2:26])C>CN(C)C=O>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]3[O:18][N:26]=[C:23]([CH3:22])[N:19]=3)=[C:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 30926N-HydroxyacetamidineHCID 13987111HCID 13987111, compound

Product 1

HCID 14590409HCID 14590409, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.30 g (30.2 mmol) of 1-[(5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)carbonyl]imidazole are suspended in 60 ml of N,N-dimethylformamide and the suspension is treated with 3.0 g (40.5 mmol) of acetamidoxime. After stirring at 60° for 5.5 hours the mixture is evaporated to dryness, 70 ml of glacial acetic acid are added to the residue and the solution is heated to 120° for 2.5 hours. The solution is then evaporated and the residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic phase is separated, dried over magnesium sulphate and evaporated. By recrystallization of the residue from methylene chloride and ethyl acetate there is obtained 4,5-dihydro-5-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 257°-260°.

Workup

  1. customis evaporated to dryness, 70 ml of glacial acetic acid
  2. additionare added to the residue
  3. temperaturethe solution is heated to 120° for 2.5 hours
  4. customThe solution is then evaporated
  5. customthe residue is partitioned between methylene chloride and saturated sodium bicarbonate solution
  6. customThe organic phase is separated
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customBy recrystallization of the residue from methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-d6102184af3248deaeb025e9b8d9ce49
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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