N'-Hydroxycyclopropanecarboximidamide → 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-8-fluoro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 867545Notes

Reaction equation

HRID 867545 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([N:17]4C=C[N:19]=[CH:18]4)=[O:16])=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1.[CH:25]1(C(=NO)N)[CH2:27][CH2:26]1>CN(C)C=O>[CH:25]1([C:18]2[N:17]=[C:15]([C:14]3[N:13]=[CH:12][N:11]4[C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:24][C:6]=5[C:7](=[O:23])[N:8]([CH3:22])[CH2:9][C:10]=34)[O:16][N:19]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 139871131-[(8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)carbonyl]imidazole

Product 1

HCID 212899713-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-8-fluoro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.5 g (20 mmol) of 1-[(8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)carbonyl]imidazole are stirred at 100° for 1 hour together with 2.2 g (22 mmol) of cyclopropanecarboxamidoxime in 25 ml of N,N-dimethylformamide. The mixture is then evaporated to dryness, 50 ml of glacial acetic acid are added to the residue and the mixture is heated to reflux for 1 hour. The mixture is again evaporated to dryness in vacuo and the residue is dissolved in methylene chloride. The methylene chloride solution is washed twice with sodium bicarbonate solution, subsequently dried with magnesium sulphate and evaporated. By recrystallization from methylene chloride/ethyl acetate there is obtained 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-8-fluoro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 216°-217°.

Workup

  1. customThe mixture is then evaporated to dryness, 50 ml of glacial acetic acid
  2. additionare added to the residue
  3. temperaturethe mixture is heated
  4. temperatureto reflux for 1 hour
  5. customThe mixture is again evaporated to dryness in vacuo
  6. dissolutionthe residue is dissolved in methylene chloride
  7. washThe methylene chloride solution is washed twice with sodium bicarbonate solution
  8. dry with materialsubsequently dried with magnesium sulphate
  9. customevaporated
  10. customBy recrystallization from methylene chloride/ethyl acetate there

Sources & evidence

ORD record
ord-c423bafe78c54cb4828e81eb694b843d
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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