Allyl bromide → (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one

HRID 1377997노트

반응식

HRID 1377997 반응식
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][CH2:26][C@H:13]4[C:12]=23)[N:4]=1.N12CCCN=C1CC[CH2:30][CH2:29][CH2:28]2.[CH2:38](Br)[CH:39]=[CH2:40]>CN(C)C=O>[CH2:30]([N:1]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][CH2:26][C@H:13]4[C:12]=23)[N:4]=1)[CH2:40][CH:39]=[CH2:38])[CH:29]=[CH2:28]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54321795(S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

생성물 1

HCID 22876602(S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one수율 49.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3.0 g (8.1 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, 20 ml of N,N-dimethylformamide, 3 ml (20 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (1.5-5) and 6.54 g (54 mmol) of allyl bromide were stirred at 40° overnight. The reaction mixture was concentrated, the residue was dissolved in methylene chloride and the solution was washed with water. After drying the product was purified by chromatography on silica gel while eluting with melthylene chloride/methanol 19/1. There were obtained 1.8 g (49%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one, which was converted into the hydrochloride.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe solution was washed with water
  4. customAfter drying the product
  5. customwas purified by chromatography on silica gel
  6. washwhile eluting with melthylene chloride/methanol 19/1

출처 및 근거

ORD 기록
ord-1c7ef71e1d2942b289c083bc8ad2cc4d
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665718

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