(S)-1-[5-(BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one → (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

HRID 1377984Notes

Reaction equation

HRID 1377984 reaction equation
C([CH:8]([NH2:32])[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][C@H:19]4[C:18]=23)[N:10]=1)(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[NH2:32][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][C@H:19]4[C:18]=23)[N:10]=1

Participants

3

Reactant 1

HCID 70076071(S)-1-[5-(BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Product 1

HCID 53931165(S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-oneYield 81.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4.40 g (10 mmol) of (S)-1-[5-(BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were stirred for 2 hours in 20 ml of trifluoroacetic acid. The solution was concentrated, the residue was taken up in water and the aqueous solution was washed twice with methylene chloride. The aqueous phase was made alkaline with 25% ammonia and extracted seven times with methylene chloride. After drying and evaporating the combined organic phases there were obtained 2.77 g (81%) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 195°-198°, which was converted into the hydrochloride of m.p. 275°.

Workup

  1. concentrationThe solution was concentrated
  2. washthe aqueous solution was washed twice with methylene chloride
  3. extractionextracted seven times with methylene chloride
  4. customAfter drying
  5. customevaporating the combined organic phases

Sources & evidence

ORD record
ord-59055b82049e44b1bfd2bf433ab86c02
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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