N'-Hydroxycyclopropanecarboximidamide → HCID 53634253, compound

HRID 867543Notes

Reaction equation

HRID 867543 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[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:26]1(C(=NO)N)[CH2:28][CH2:27]1>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:25])[N:9]3[CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][N:20]=[C:19]([CH:26]4[CH2:28][CH2:27]4)[N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 53836693HCID 53836693, compound

Product 1

HCID 53634253HCID 53634253, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.0 g (42 mmol) of 1-[[(S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-1-yl]carbonyl]imidazole are dissolved in 60 ml of N,N-dimethylformamide, whereupon the solution is treated with 4.60 g (46 mmol) of cyclopropanecarboxamidoxime and the mixture is heated to 100° for 2 hours. The mixture is evaporated to dryness, the residue is treated with 50 ml of acetic acid and the mixture is stirred at 115° for 2 hours. After evaporation of the solvent the residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic phase is separated, dried over magnesium sulphate and concentrated. The residue is chromatographed on silica gel while eluting with ethyl acetate. After recrystallization from ethyl acetate there is obtained (S)-8-chloro-1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of melting point 140°-142°.

Workup

  1. temperaturethe mixture is heated to 100° for 2 hours
  2. customThe mixture is evaporated to dryness
  3. additionthe residue is treated with 50 ml of acetic acid
  4. customAfter evaporation of the solvent the residue
  5. customis partitioned between methylene chloride and saturated sodium bicarbonate solution
  6. customThe organic phase is separated
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica gel
  10. washwhile eluting with ethyl acetate
  11. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-c1d29b5bcb9e4f8eb1537134257cf8d8
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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