Water → 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1606954

반응식

HRID 1606954 반응식
[Cl:1][C:2]1[C:7]2[CH2:8][N:9]([CH3:20])[CH2:10][C:11]3[N:12]([C:13](=O)[NH:14][C:15]=3/[CH:16]=[CH:17]\Cl)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[OH2:32]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:32])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[CH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867433567-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine--one

생성물 1

HCID 198515337-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

20.2 g (65.5 mmol) of 7-chloro-3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine--one was heated to boiling under reflux for 5 hours together with 11.7 ml (78.5 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene in 200 ml of N,N-dimethylformamide. The reaction mixture was subsequently poured into 800 ml of water and extracted four time with methylene chloride. The organic extracts were washed four times with water, dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel while eluting with ethyl acetate and two successive crystallizations from acetonitrile and from ethyl acetate there was obtained 7-chloro-3-ethynyl-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 201°-202°.

후처리

  1. extractionextracted four time with methylene chloride
  2. washThe organic extracts were washed four times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. washAfter chromatography of the residue on silica gel while eluting with ethyl acetate and two successive crystallizations from acetonitrile and from ethyl acetate

출처 및 근거

ORD 기록
ord-cbbe1afd9e4849a7a994b5b2448f4990
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863920

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