HCID 22876606, compound → HCID 54047026, compound

HRID 1378019Notes

Reaction equation

HRID 1378019 reaction equation
C([NH:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]2[N:16]=[CH:17][N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:23]=4[C:22](=[O:33])[N:21]4[CH2:34][CH2:35][C@H:20]4[C:19]=23)[N:11]=1)(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[NH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]2[N:16]=[CH:17][N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([F:32])([F:31])[F:30])[C:23]=4[C:22](=[O:33])[N:21]4[CH2:34][CH2:35][C@H:20]4[C:19]=23)[N:11]=1

Participants

3

Reactant 1

HCID 22876606HCID 22876606, compound

Product 1

HCID 54047026HCID 54047026, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7.8 g (15.9 mmol) of crude (S)-1-[5-(N-BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-8-trifluoromethyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one and 30 ml of trifluoroacetic acid were stirred at room temperature for 1hour. The solution was evaporated. The residue was dissolved in water and washed three times with methylene chloride. The aqueous phase was made alkaline with conc. ammonia and extracted nine times with ethyl acetate (a total of about 1 I). By evaporating the organic phases, combined and dried over magnesium sulfate, there were obtained 4.57 g (73%) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-trifluoromethyl-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. washwashed three times with methylene chloride
  4. extractionextracted nine times with ethyl acetate (a total of about 1 I)
  5. customBy evaporating the organic phases
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-02e0877f33e8485f958622c80cd38d0b
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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