Water → (Z)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

HRID 55995

반응식

HRID 55995 반응식
[CH:1]1([CH2:4][O:5]/[N:6]=[C:7](/[C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][N:11]=2)\[CH2:8][NH2:9])[CH2:3][CH2:2]1.C(N(CC)CC)C.[F:28][C:29]([F:40])([F:39])[C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].O>ClCCl>[Cl:16][C:15]1[C:10](/[C:7](=[N:6]/[O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)/[CH2:8][NH:9][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=2[C:29]([F:28])([F:39])[F:40])=[N:11][CH:12]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 118071502(2E)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-2-(cyclopropylmethoxyimino)ethanamine

생성물 1

HCID 118071512(Z)-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-(cyclopropylmethoxyimino)ethyl]-2-(trifluoromethyl)benzamide수율 94.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a solution of 65 mg of (E)-2-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone-O-(cyclopropylmethyl)oxime and 32 mg of triethylamine in 2 ml of dichloromethane, 39 mg of 2-(trifluoromethyl)benzoyl chloride was added dropwise with stirring under cooling with ice, and after the addition, the mixture was stirred at room temperature for another 1 hour. After completion of the reaction, the reaction mixture was mixed with 2 ml of water and extracted with dichloromethane (2 ml×1), the resulting organic layer was dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (with a gradient of from 2:18 to 5:15) as the eluent to obtain 85 mg of the desired product as white crystals.

후처리

  1. temperatureunder cooling with ice
  2. additionafter the addition
  3. stirringthe mixture was stirred at room temperature for another 1 hour
  4. customAfter completion of the reaction
  5. extractionextracted with dichloromethane (2 ml×1)
  6. dry with materialthe resulting organic layer was dried over saturated aqueous sodium chloride
  7. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.)

출처 및 근거

ORD 기록
ord-ce3353de775042cdbc0a243cba669183
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434684B2

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