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

HRID 17370

반응식

HRID 17370 반응식
C[Al](C)C.Cl.[CH3:6][NH2:7].C([O:10][C:11]([C:13]1[O:14][C:15]2[C:21]([F:22])=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]([CH3:29])=[C:18]([C:30]#[N:31])[C:16]=2[N:17]=1)=O)C.Cl>ClCCl>[C:30]([C:18]1[C:16]2[N:17]=[C:13]([C:11]([NH:7][CH3:6])=[O:10])[O:14][C:15]=2[C:21]([F:22])=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]=1[CH3:29])#[N:31]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6364545Methylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

생성물 1

HCID 510423344-Cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide수율 64%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 1.80 ml, 1.85 mmol) was dropwise added to a dichloromethane (2 ml) solution of methylamine hydrochloride (125 mg, 1.85 mmol) at room temperature, and stirred for 40 minutes. Subsequently, a dichloromethane (2 ml) solution of ethyl-4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (200 mg, 617 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 dichloromethane/methanol (100:1, v/v) gave the entitled compound (122 mg, 64%) as a pale green 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-f4efe491a1dc466fabeceab2ce125842
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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