4-Fluoro-3-(trifluoromethyl)benzoyl Chloride → 4-Fluoro-N-{5-[4-(pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-yl}-3-(trifluoromethyl)-benzamide

HRID 387482

반응식

HRID 387482 반응식
Br.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[O:19][C:18]([NH2:20])=[N:17][N:16]=3)=[CH:11][CH:10]=2)[CH:3]=1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][C:23]=1[C:31]([F:34])([F:33])[F:32]>N1C=CC=CC=1.CO>[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:20][C:18]2[O:19][C:15]([C:12]3[CH:11]=[CH:10][C:9]([O:8][C:4]4[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=4)=[CH:14][CH:13]=3)=[N:16][N:17]=2)=[O:27])=[CH:24][C:23]=1[C:31]([F:32])([F:33])[F:34]

참가 물질

5

반응물 2

HCID 1442534-Fluoro-3-(trifluoromethyl)benzoyl ChlorideHCID 686796585-[4-(Pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-amine hydrobromide salt

생성물 1

HCID 591354204-Fluoro-N-{5-[4-(pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-yl}-3-(trifluoromethyl)-benzamide수율 47.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1049Pyridine용매

실험 절차

5-[4-(Pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-amine hydrobromide salt (167.5 mg, 0.5 mmol) was suspended in 2 mL of anhydrous pyridine. Neat 4-fluoro-3-trifluoromethylbenzoyl chloride (200 uL) was added directly into the solution. It was left to stir for 18 hours. The reaction mixture formed a red solution with a yellow precipitate. Then it was diluted with ca. 1 mL of MeOH, filtered through 0.22 u syringe filter and purified by reverse phase preparative HPLC using acetonitrile/water mixture containing 0.01% of TFA. Fractions, containing the product, were combined and partitioned between ca. 40 mL of EtOAc and ca. 40 mL of saturated aqueous NaHCO3. The EtOAc layer was washed with brine, dried over anhydrous sodium sulfate and filtered. Solvent was removed in vacuo to give the title product as a yellow solid (105.1 mg). Yield 47.3%.

후처리

  1. waitIt was left
  2. customThe reaction mixture formed a red solution with a yellow precipitate
  3. filtrationfiltered through 0.22 u syringe
  4. filtrationfilter
  5. custompurified by reverse phase preparative HPLC
  6. additioncontaining 0.01% of TFA
  7. additionFractions, containing the product
  8. custompartitioned between ca. 40 mL of EtOAc and ca. 40 mL of saturated aqueous NaHCO3
  9. washThe EtOAc layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customSolvent was removed in vacuo

출처 및 근거

ORD 기록
ord-cb6ec36528c041d79eb19b6d9d9666b6
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372971B2

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