Potassium Carbonate → N'-benzyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide

HRID 1475193노트

반응식

HRID 1475193 반응식
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([C:15]([O:17]CC)=O)[O:12][N:11]=2)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl.[CH2:30]([NH:37][NH2:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:30]([NH:37][NH:38][C:15]([C:13]1[O:12][N:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=2)[N:14]=1)=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 146540Benzylhydrazine dihydrochlorideHCID 86711474Ethyl 3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole-5-carboxylate2회

생성물 1

HCID 86711886N'-benzyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide수율 40.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a suspension of ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate (Intermediate A) (1.0 g, 3.3 mmol) and K2CO3 (1.1 g, 13 mmol) in THF (17 mL) was added benzylhydrazine dihydrochloride (780 mg, 5.0 mmol). The mixture was heated to 70° C. for 3 h. The mixture was cooled to RT, filtered (Celite), and concentrated under reduced pressure. The crude oil was purified by Biotage (5% EtOAc/Hexane—60% EtOAc) to provide a white solid (500 mg, 40%): MS (ES+) C17H13F3N4O3 requires: 378. found: 379 [M+H]+.

후처리

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered (Celite)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude oil was purified by Biotage (5% EtOAc/Hexane—60% EtOAc)

출처 및 근거

ORD 기록
ord-25e832fad5c34ebe81454731e4c91f05
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018380B2

반응 노트

불러오는 중…