N'-Hydroxycyclopropanecarboximidamide → Ro 19-0528

HRID 867542Notes

Reaction equation

HRID 867542 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.[CH:25]1(C(=NO)N)[CH2:27][CH2:26]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]([CH:25]4[CH2:27][CH2:26]4)[N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 13987114HCID 13987114, compound

Product 1

HCID 192288Ro 19-0528

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15 g (43.8 mmol) of 1-[[7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl]carbonyl]imidazole, 6.60 g (65.8 mmol) of cyclopropanecarboxamidoxime and 100 ml of N,N-dimethylformamide are stirred at 70° for 1.5 hours, whereupon the mixture is evaporated to dryness, 100 ml of glacial acetic acid are added to the residue and the solution is heated to 120° for 1.5 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 7-chloro-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 183°-184°.

Workup

  1. customis evaporated to dryness, 100 ml of glacial acetic acid
  2. additionare added to the residue
  3. temperaturethe solution is heated to 120° for 1.5 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-e2339273fde44cd6b41158607bb1170d
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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