N'-Hydroxycyclopropanecarboximidamide → 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 867554Notes

Reaction equation

HRID 867554 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]([OH:19])=O)=[C:4]2[CH2:3]1.[CH:20]1([C:23](=[N:25]O)[NH2:24])[CH2:22][CH2:21]1>CN(C)C=O>[CH:20]1([C:23]2[N:25]=[C:17]([C:16]3[N:15]=[CH:14][N:5]4[C:6]5[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=5[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=34)[O:19][N:24]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 103326765-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

Product 1

HCID 148537083-(3-cyclopropyl-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

A mixture of 9.77 g (39 mmol) of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, 40 ml of N,N-dimethylformamide and 6.48 g (40 mmol) of N,N'-carbonyldiimidazole is stirred at 100° for 1 hour. 4.01 g (40 mmol) of cyclopropanecarboxamidoxime are subsequently added thereto and the mixture is stirred at 100° for a further 4 hours. The mixture is then evaporated and the residue is heated to 115° for 4 hours with 100 ml of acetic acid. The solution is evaporated to dryness 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 from methylene chloride and ethyl acetate there is obtained 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 202°-203°.

Workup

  1. stirringthe mixture is stirred at 100° for a further 4 hours
  2. customThe mixture is then evaporated
  3. temperaturethe residue is heated to 115° for 4 hours with 100 ml of acetic acid
  4. customThe solution is evaporated to dryness
  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 from methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-abb5904913494f308ba642c7104dd9bd
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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