HCID 70076854, compound → HCID 53773985, compound

HRID 1378142Notes

Reaction equation

HRID 1378142 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:28])=[CH:27][C:22]=4[C:21](=[O:29])[N:20]4[CH2:30][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]>[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:28])=[CH:27][C:22]=4[C:21](=[O:29])[N:20]4[CH2:30][CH2:31][CH2:32][C@H:19]4[C:18]=23)[N:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 70076854HCID 70076854, compound

Product 1

HCID 53773985HCID 53773985, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.96 g (4.1 mmol) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-11,1 2,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one were dissolved in 25 ml of ethyl acetate and hydrogenated at normal pressure and room temperature in the presence of 37 mg of 5% palladium-charcoal. The catalyst was separated and the solution was evaporated. By chromatography of the residue on silica gel while eluting with ethyl acetate there were obtained 1.49 g (83%) of (S)-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-11,12,13, 13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 222°-225°.

Workup

  1. customThe catalyst was separated
  2. customthe solution was evaporated
  3. washBy chromatography of the residue on silica gel while eluting with ethyl acetate

Sources & evidence

ORD record
ord-9af2194d33154fe292d4c0e8c28c5eba
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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