Hydrochloric Acid → 7-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-4-carbonitrile

HRID 17379

반응식

HRID 17379 반응식
C[Al](C)C.[NH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:11]([C:13]1[C:18]2[N:19]=[C:20]([C:22](OCC)=[O:23])[O:21][C:17]=2[C:16]([F:27])=[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]=1[CH3:34])#[N:12].Cl>ClCCl>[F:27][C:16]1[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:14]([CH3:34])[C:13]([C:11]#[N:12])=[C:18]2[C:17]=1[O:21][C:20]([C:22]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:23])=[N:19]2

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 16682925TrimethylaluminumHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

생성물 1

HCID 685850607-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-4-carbonitrile수율 37%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 898 μl, 925 μmol) was dropwise added to a dichloromethane (1 ml) solution of piperidine (92 μl, 925 μmol) at room temperature, and stirred for 15 minutes. Subsequently, a dichloromethane (2 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (150 mg, 463 μl) was dropwise added and stirred for 63 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature. The reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with n-hexane/ethyl acetate (4:1, v/v) gave the entitled compound (62 mg, 37%) as a white solid.

후처리

  1. stirringstirred for 63 hours
  2. additionwas added to the reaction liquid
  3. temperaturewith cooling with ice
  4. stirringby stirring at room temperature
  5. customThe reaction liquid
  6. extractionwas extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-40e22b4816854e87bb5bed1d0b4d7be8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

연결된 노트

불러오는 중…