1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(1-methyl-1H-imidazol-4-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole

HRID 517567

반응식

HRID 517567 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3]1.O[NH:11][C:12](=[NH:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[O:9][N:24]=[C:12]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=3)[N:11]=2)[N:4]=[CH:3]1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 27333094-(Trifluoromethoxy)benzamidoxime

생성물 1

HCID 867115075-(1-methyl-1H-imidazol-4-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole수율 48.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

To a solution of 1-methyl-1H-imidazole-4-carboxylic acid (1.5 g, 11.9 mmol) in DMF (30 mL), N-hydroxy-4-(trifluoromethoxy)benzimidamide (3.1 g, 14.3 mmol), HOBT (2.2 g, 14.3 mmol) and EDCI (2.7 g, 14.3 mmol) were added in sequence. The mixture was stirred at 140° C. overnight, then cooled to RT, quenched by water (100 mL), and extracted with EtOAc (2×50 mL). The combined organic phases were washed by water (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by silica gel column chromatography (EtOAc:Petroleum ether=1:5) to give 5-(1-methyl-1H-imidazol-4-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole as a white solid (1.8 g, 40.0%). MS (ES+) C13H9F3N4O2 requires: 310, found: 311 [M+H]+.

후처리

  1. temperaturecooled to RT
  2. customquenched by water (100 mL)
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic phases were washed by water (3×50 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude product, which
  9. customwas purified by silica gel column chromatography (EtOAc:Petroleum ether=1:5)

출처 및 근거

ORD 기록
ord-668076e232bb4927bba027a88a3c5d40
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115120B2

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