HCID 54137505, compound → HCID 53735413, compound

HRID 1378130Notes

Reaction equation

HRID 1378130 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][CH:26]=[CH:27][C:22]=4[C:21](=[O:28])[N:20]4[CH2:29][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]>[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][CH:26]=[CH:27][C:22]=4[C:21](=[O:28])[N:20]4[CH2:29][CH2:30][CH2:31][C@H:19]4[C:18]=23)[O:11][N:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 54137505HCID 54137505, compound

Product 1

HCID 53735413HCID 53735413, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.8 g (4 mmol) of (S)-1-(3-diallylaminomethyl-1,2,4-oxadiazol-5-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one were dissolved in 50 ml of methanol and hydrogenated at normal pressure and room temperature in the presence of 60 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 methylene chloride/methanol 19.5/0.5 there was obtained 1 g (60%) of (S)-1-(3-dipropylaminomethyl-1,2,4-oxadiazol-5-yl)-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. 198°-201°.

Workup

  1. customThe catalyst was separated
  2. customthe solution was evaporated
  3. washBy chromatography of the residue on silica gel while eluting with methylene chloride/methanol 19.5/0.5 there

Sources & evidence

ORD record
ord-d2ef968543044135b5c8b8845b11a0da
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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