HCID 54418996, compound → HCID 54050108, compound

HRID 1378039Notes

Reaction equation

HRID 1378039 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[N:13]=[C:12]([C:14]2[N:15]=[CH:16][N:17]3[C:23]4[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=4[C:21](=[O:29])[N:20]4[CH2:30][CH2:31][C@H:19]4[C:18]=23)[O:11][N:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]>CO.[Pd]>[F:28][C:26]1[CH:25]=[CH:24][C:23]2[N:17]3[CH:16]=[N:15][C:14]([C:12]4[O:11][N:10]=[C:9]([CH2:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])[N:13]=4)=[C:18]3[C@@H:19]3[CH2:31][CH2:30][N:20]3[C:21](=[O:29])[C:22]=2[CH:27]=1

Participants

4

Reactant 1

HCID 54418996HCID 54418996, compound

Product 1

HCID 54050108HCID 54050108, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1 g (2.2 mmol) of (S)-1-(3-diallylaminomethyl-1,2,4-oxadiazol-5-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 5 ml of methanol were hydrogenated at room temperature and normal pressure in the presence of 22 mg of 5% palladium-on-charcoal. After separating the catalyst the residue was purified by chromatography on silica gel while eluting with ethyl acetate/hexane/triethylamine 17/2/1. There was obtained 0.53 g (56%) of (S)-7-fluoro-12,12a-dihydro-1-(3-di-n-propylaminomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one (oil: Rf. 0.36; Kieselgel 60 F254. Eluent: ethyl acetate/hexane/triethylamine 17/2/1), which was converted into the hydrochloride.

Workup

  1. customwere hydrogenated at room temperature
  2. customAfter separating the catalyst the residue
  3. customwas purified by chromatography on silica gel
  4. washwhile eluting with ethyl acetate/hexane/triethylamine 17/2/1

Sources & evidence

ORD record
ord-578b3fef0344473b83bb8909abb39307
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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