Hydrochloric Acid → 4-cyano-N-ethyl-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17574

반응식

HRID 17574 반응식
C[Al](C)C.[CH2:5]([NH:7][CH3:8])[CH3:6].[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20]([O:22]CC)=O)[O:19][C:15]=2[C:14]([F:25])=[C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]=1[CH3:32])#[N:10].Cl>ClCCl>[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20]([N:7]([CH2:5][CH3:6])[CH3:8])=[O:22])[O:19][C:15]=2[C:14]([F:25])=[C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:12]=1[CH3:32])#[N:10]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 12219N-MethylethylamineHCID 16682925TrimethylaluminumHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

생성물 1

HCID 685857964-cyano-N-ethyl-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide수율 87.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution) (2.40 ml, 2.47 mmol) was dropwise added at room temperature to a dichloromethane (8 ml) solution of N-ethylmethylamine (146 mg, 2.47 mmol), followed by stirring for 80 minutes. Subsequently, a dichloromethane (4 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (400 mg, 1.23 mmol) was dropwise added, followed by stirring for 19 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, then the reaction liquid was extracted with chloroform. Next, the combined organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (362 mg, 87%) as a white solid.

후처리

  1. stirringby stirring for 19 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 materialNext, the combined organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

출처 및 근거

ORD 기록
ord-ef64666c597e4f18a4fedb397d401a01
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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