HCID 22876572, compound → (S)-8-chloro-7-fluoro-12,12a-dihydro-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

HRID 1378006Notes

Reaction equation

HRID 1378006 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[O:13][N:12]=[C:11]([C:14]2[N:15]=[CH:16][N:17]3[C:23]4[CH:24]=[CH:25][C:26]([F:29])=[C:27]([Cl:28])[C:22]=4[C:21](=[O:30])[N:20]4[CH2:31][CH2:32][C@H:19]4[C:18]=23)[N:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[Cl:28][C:27]1[C:22]2[C:21](=[O:30])[N:20]3[CH2:31][CH2:32][C@H:19]3[C:18]3[N:17]([CH:16]=[N:15][C:14]=3[C:11]3[N:10]=[C:9]([CH2:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])[O:13][N:12]=3)[C:23]=2[CH:24]=[CH:25][C:26]=1[F:29]

Participants

4

Reactant 1

HCID 22876572HCID 22876572, compound

Product 1

HCID 53845017(S)-8-chloro-7-fluoro-12,12a-dihydro-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-oneYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.27 g (5 mmol) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were hydrogenated in 80 ml of ethyl acetate in the presence of 35 mg of 5% palladium-on-charcoal at room temperature and normal pressure. After separating the catalyst the reaction mixture was purified by chromatography on silica gel while eluting with ethyl acetate. There were obtained 1.83 g (80%) of (S)-8-chloro-7-fluoro-12,12a-dihydro-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride.

Workup

  1. customAfter separating the catalyst the reaction mixture
  2. customwas purified by chromatography on silica gel
  3. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-8dc6b500091b4744af6cbc95d1208f6f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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