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Dimethylformamide → 3-ethynyl-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606959
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HRID 1606959 반응식
Cl/[CH:2]=[CH:3]\[C:4]1[N:5]=[CH:6][N:7]2[C:13]3[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=3[C:11](=[O:19])[N:10]([CH3:20])[CH2:9][C:8]=12.N12CCCN=C1CCCCC2.CN(C)C=O>O>[C:3]([C:4]1[N:5]=[CH:6][N:7]2[C:13]3[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=3[C:11](=[O:19])[N:10]([CH3:20])[CH2:9][C:8]=12)#[CH:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867433583-[(Z)-2-chlorovinyl]-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

생성물 1

HCID 198515463-ethynyl-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

시약·촉매·용매 1

HCID 962Water용매

실험 절차

3.70 g (12.7 mmol) of 3-[(Z)-2-chlorovinyl]-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to boiling under reflux for 4 hours together with 2.26 ml (15.2 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene 30 ml of N,N-dimethylformamide. The reaction mixture was subsequently poured into 400 ml of water and extracted five times with methylene chloride. The organic extracts were washed four times with water, dried over magnesium sulphate and evaporated. The residue was dissolved in ethyl acetate, treated with charcoal and recrystallized from ethyl acetate. There was obtained 3-ethynyl-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-6-one of melting point 207°-208°.

후처리

  1. extractionextracted five times with methylene chloride
  2. washThe organic extracts were washed four times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. additiontreated with charcoal
  7. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-cb31e1cdbafa47bab0b2d74ccb3dcb1a
출처 데이터셋
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04863920

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