N'-Hydroxycyclopropanecarboximidamide → HCID 21289948, compound

HRID 867556Notes

Reaction equation

HRID 867556 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([OH:18])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:21]1([C:24](=[N:26]O)[NH2:25])[CH2:23][CH2:22]1>CN(C)C=O>[Br:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:18][N:26]=[C:24]([CH:21]4[CH2:23][CH2:22]4)[N:25]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 22914630HCID 22914630, compound

Product 1

HCID 21289948HCID 21289948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.2 g (18 mmol) of 7-bromo-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid in 90 ml of N,N-dimethylformamide are stirred at 70° for 2.5 hours with 2.92 g (18 mmol) of N,N'-carbonyldiimidazole. 1.80 g (18 mmol) of cyclopropanecarboxamidoxime are subsequently added thereto and the mixture is stirred at 100° for a further 2 hours. The solution is evaporated, the residue is treated with 70 ml of acetic acid and the mixture is stirred at 120° for 5 hours. The reaction mixture is evaporated and the residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulphate and evaporated. By chromatography on silica gel while eluting with ethyl acetate and recrystallization from acetonitrile there is obtained 7-bromo-4,5-dihydro-3-(3-cyclopropyl-1,2,4-oxadiazol-5yl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 187°-189°.

Workup

  1. customThe solution is evaporated
  2. additionthe residue is treated with 70 ml of acetic acid
  3. stirringthe mixture is stirred at 120° for 5 hours
  4. customThe reaction mixture is evaporated
  5. customthe residue is partitioned between methylene chloride and saturated sodium bicarbonate solution
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. customevaporated
  8. washBy chromatography on silica gel while eluting with ethyl acetate and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-fa5c7cedcc6d43499bc42e89738d30da
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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