N'-hydroxypentanimidamide → (S)-1-(3-butyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

HRID 867549Notes

Reaction equation

HRID 867549 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][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.[C:27](=NO)(N)[CH2:28][CH2:29][CH2:30]C>CN(C)C=O>[CH2:27]([C:19]1[N:18]=[C:16]([C:15]2[N:14]=[CH:13][N:12]3[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=4[C:8](=[O:26])[N:9]4[CH2:25][CH2:24][CH2:23][C@H:10]4[C:11]=23)[O:17][N:20]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 4136427N'-hydroxypentanimidamideHCID 54332091(S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

Product 1

HCID 54206484(S)-1-(3-butyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.0 g (30 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole are dissolved in 50 ml of N,N-dimethylformamide, whereupon the solution is treated with 3.96 g (34 mmol) of valeramidoxime and the mixture is heated to 85° for 3 hours. The reaction mixture is evaporated to dryness. The residue is dissolved in 50 ml of glacial acetic acid and the mixture is stirred at 110° for 2 hours. The reaction mixture is subsequently evaporated and the residue is chromatographed on silica gel while eluting with ethyl acetate. After evaporation of the eluate there is obtained (S)-1-(3-butyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 181°-182°.

Workup

  1. temperaturethe mixture is heated to 85° for 3 hours
  2. customThe reaction mixture is evaporated to dryness
  3. dissolutionThe residue is dissolved in 50 ml of glacial acetic acid
  4. customThe reaction mixture is subsequently evaporated
  5. customthe residue is chromatographed on silica gel
  6. washwhile eluting with ethyl acetate
  7. customAfter evaporation of the eluate there

Sources & evidence

ORD record
ord-27ed0bdd9c624dd8be4dd63f6407c4ea
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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