Dimethylformamide → 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378044노트

반응식

HRID 1378044 반응식
[C:1](NCC(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:13](N1C=CN=C1)([N:15]1C=CN=C1)=O.[Cl:25][C:26]1[C:31]2[C:32](=[O:45])[N:33]([CH3:44])[CH2:34][C:35]3[N:36]([CH:37]=[N:38][C:39]=3[C:40](=[N:42][OH:43])[NH2:41])[C:30]=2[CH:29]=[CH:28][CH:27]=1.[CH3:46]N(C)C=O>>[C:1]([C:46]1[O:43][N:42]([CH2:13][NH2:15])[CH:40]([C:39]2[N:38]=[CH:37][N:36]3[C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:25])[C:31]=4[C:32](=[O:45])[N:33]([CH3:44])[CH2:34][C:35]=23)[N:41]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 541588047-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

생성물 1

HCID 677135773-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one수율 96%

실험 절차

2.45 g (14 mmol) of BOC-glycine were dissolved in 20 ml of N,N-dimethylformamide, whereupon the mixture was treated portionwise with 2.43 g (15 mmol) of 1,1'-carbonyldiimidazole and stirred at 50° for 20 min. After adding 3.8 g (12.4 mmol) of 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime the mixture was stirred at 90° overnight. The reaction mixture was concentrated; the residue was dissolved in methylene chloride and washed three times with water. After drying the solution, evaporation of the solvent and crystallization of the residue from ethyl acetate and hexane there were obtained 5.33 g (96%) of 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 144°-146°.

후처리

  1. stirringwas stirred at 90° overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed three times with water
  5. customAfter drying
  6. customthe solution, evaporation of the solvent and crystallization of the residue from ethyl acetate

출처 및 근거

ORD 기록
ord-f96b7f12d8824bdbb604f11449c8e8ca
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665718

반응 노트

불러오는 중…