HCID 67713734, compound → (S)-1-(5-aminomethyl-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

HRID 1377993Notes

Reaction equation

HRID 1377993 reaction equation
C([CH:8]([NH2:33])[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)(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[NH2:33][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

Participants

3

Reactant 1

HCID 67713734HCID 67713734, compound

Product 1

HCID 53982526(S)-1-(5-aminomethyl-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-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

36.8 g (77.5 mmol) of crude (S)-1-[5-(BOC-aminomethyl)-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 and 90 ml of trifluoroacetic acid were stirred at room temperature for 2 hours. The solution was evaporated, the residue was dissolved in water and the aqueous solution was washed three times with methylene chloride. The aqueous phase was made alkaline with conc. ammonia and extracted eight times with methylene chloride (a total of about 1 l). By evaporating the organic phases, combined and dried over magnesium sulfate, there were obtained 23.8 g (82%) of (S)-1-(5-aminomethyl-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, which was used without further purification as the starting material for the Example described hereinafter.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in water
  3. washthe aqueous solution was washed three times with methylene chloride
  4. extractionextracted eight times with methylene chloride (a total of about 1 l)
  5. customBy evaporating the organic phases
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-e2cffca53de244488baad6c62b73b4d3
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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