Chloroacetic anhydride → 7-Chloro-3-(5-chloromethyl-[1,2,4]oxadiazol-3-yl)-5-methyl-4,5-dihydro-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378147노트

반응식

HRID 1378147 반응식
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:18][OH:19])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:22][CH2:23][C:24](OC(=O)CCl)=O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:17]=[C:24]([CH2:23][Cl:22])[O:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 10946Chloroacetic anhydrideHCID 541588047-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

생성물 1

HCID 224621917-Chloro-3-(5-chloromethyl-[1,2,4]oxadiazol-3-yl)-5-methyl-4,5-dihydro-imidazo[1,5-a][1,4]benzodiazepin-6-one수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

9.8 g (32 mmol) of 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime were stirred in 60 ml of N,N-dimethylformamide with 7 g (41 mmol) of chloroacetic anhydride at room temperature for 1 hour and at 105° for 4 hours. After evaporating the solvent the residue was dissolved in methylene chloride and the solution was washed with saturated sodium bicarbonate solution and dried over magnesium sulfate. By evaporation of the solvent and chromatography of the residue on silica gel while eluting with ethyl acetate there were obtained 6.63 g (65%) of 7-chloro-3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-6-one.

후처리

  1. customAfter evaporating the solvent the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customBy evaporation of the solvent and chromatography of the residue on silica gel
  6. washwhile eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-57e0db0a84dd4197a4af1631fa09a7e7
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665718

반응 노트

불러오는 중…