Hydrochloric Acid → 6-Bromo-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide

HRID 17393

반응식

HRID 17393 반응식
C[Al](C)C.Cl.[CH3:6][NH:7][CH3:8].[Br:9][C:10]1[C:23]([CH3:24])=[C:22]([C:25]#[N:26])[C:13]2[N:14]=[C:15]([C:17]([O:19]CC)=O)[O:16][C:12]=2[C:11]=1[F:27].Cl>ClCCl>[Br:9][C:10]1[C:23]([CH3:24])=[C:22]([C:25]#[N:26])[C:13]2[N:14]=[C:15]([C:17]([N:7]([CH3:8])[CH3:6])=[O:19])[O:16][C:12]=2[C:11]=1[F:27]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 16682925TrimethylaluminumHCID 68584335Ethyl 6-bromo-4-cyano-7-fluoro-5-methyl-1,3-benzoxazole-2-carboxylate

생성물 1

HCID 685849626-Bromo-4-cyano-7-fluoro-N,N,5-trimethyl-1,3-benzoxazole-2-carboxamide수율 48%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 57.9 ml, 59.6 mmol) was dropwise added to a dichloromethane (100 ml) solution of dimethylamine hydrochloride (4.86 g, 59.6 mmol) with cooling in a water bath, taking 30 minutes, and stirred for 65 minutes at room temperature. Subsequently, a dichloromethane (30 ml) solution of ethyl 6-bromo-4-cyano-7-fluoro-5-methyl-1,3-benzoxazole-2-carboxylate (I-126) (6.50 g, 19.9 mmol) was dropwise added and stirred for 30 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, and 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 (3.10 g, 48%) as a pale yellow solid. The fraction containing impurities was recovered and purified twice in the same manner to obtain the entitled compound (362 mg, 591 mg), and 4.05 g (62%) of the entitled compound was obtained in total.

후처리

  1. temperaturewith cooling in a water bath
  2. stirringstirred for 30 hours
  3. additionwas added to the reaction liquid
  4. temperaturewith cooling with ice
  5. stirringby stirring at room temperature
  6. customthe reaction liquid
  7. extractionwas extracted with chloroform
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d25f7f671b524bef9b839edaa7c4f18c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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