(S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxaldehyde-1-oxime → (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

HRID 67337

반응식

HRID 67337 반응식
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([CH:16]=[N:17]O)=[C:5]2[C@@H:4]2[CH2:19][CH2:20][CH2:21][N:3]12>C(OC(=O)C)(=O)C>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]#[N:17])=[C:5]2[C@@H:4]2[CH2:19][CH2:20][CH2:21][N:3]12

참가 물질

3

반응물 1

HCID 86738267(S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxaldehyde-1-oxime

생성물 1

HCID 53823854(S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

A solution of 5.24 g (18.5 mmol) of (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxaldehyde-1-oxime in 50 ml of acetic acid anhydride is heated to boiling under reflux for 3 hours and subsequently evaporated in vacuo. The residue is taken up in chloroform, the solution is washed once with ca 30 ml of saturated sodium hydrogen carbonate solution and once with ca 30 ml of water, dried over magnesium sulphate and evaporated. After column chromatography and recrystallisation from ethyl acetate, there is obtained (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile of melting point 223°-225° C.

후처리

  1. temperatureunder reflux for 3 hours
  2. customsubsequently evaporated in vacuo
  3. washthe solution is washed once with ca 30 ml of saturated sodium hydrogen carbonate solution and once with ca 30 ml of water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customAfter column chromatography and recrystallisation from ethyl acetate

출처 및 근거

ORD 기록
ord-d6fe4e1954cb4e55ac409977c4865172
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346030

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