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

HRID 1377982Notes

Reaction equation

HRID 1377982 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20][N:21](C(OC(C)(C)C)=O)[CH3:22])[O:17][N:16]=4)=[C:10]3[C@@H:9]3[CH2:30][CH2:31][N:8]3[C:7](=[O:32])[C:6]=2[CH:33]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20][NH:21][CH3:22])[O:17][N:16]=4)=[C:10]3[C@@H:9]3[CH2:30][CH2:31][N:8]3[C:7](=[O:32])[C:6]=2[CH:33]=1

Participants

3

Reactant 1

HCID 22876616(S)-7-fluoro-12,12a-dihydro-1-[5-(N-BOC-N-methylaminomethyl)-1,2,4-oxadiazol-3-yl]-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Product 1

HCID 22876615(S)-7-fluoro-12,12a-dihydro-1-(5-methylaminomethyl-1,2,4-oxadiazol-3-yl)-9H,11H-azeto[2,1-c]imidazo-[1,5-a][1,4]benzodiazepin-9-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7.74 g (17 mmol) of crude (S)-7-fluoro-12,12a-dihydro-1-[5-(N-BOC-N-methylaminomethyl)-1,2,4-oxadiazol-3-yl]-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were stirred for 2 hours in 25 ml of trifluoroacetic acid. The solution was concentrated, the residue was taken up in water and the solution was washed twice with methylene chloride. The aqueous phase was made alkaline with 25% ammonia and extracted seven times with methylene chloride. There were obtained 5.12 g (85%) of (S)-7-fluoro-12,12a-dihydro-1-(5-methylaminomethyl-1,2,4-oxadiazol-3-yl)-9H,11H-azeto[2,1-c]imidazo-[1,5-a][1,4]benzodiazepin-9-one of m.p. 187°-190°, which was converted into the hydrochloride of m.p. 155°-160°.

Workup

  1. concentrationThe solution was concentrated
  2. washthe solution was washed twice with methylene chloride
  3. extractionextracted seven times with methylene chloride

Sources & evidence

ORD record
ord-805d57badca84141a223a69b68c3c6d8
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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