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

HRID 55995

反応式

HRID 55995 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-ce3353de775042cdbc0a243cba669183
出典データセット
uspto-grants-2016_09
特許番号
US09434684B2

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