(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 1377982노트

반응식

HRID 1377982 반응식
[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

참가 물질

3

반응물 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

생성물 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-one수율 85%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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°.

후처리

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

출처 및 근거

ORD 기록
ord-805d57badca84141a223a69b68c3c6d8
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665718

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