Water → 3-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-trifluoroethyl-phenyl}-5-methyl-[1,2,4]oxadiazole

HRID 471376ノート

反応式

HRID 471376 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([NH:20][OH:21])=[NH:19])=[C:16]([CH3:24])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:29][C:30]([F:36])([F:35])CC(Cl)=O.O.[CH3:38][CH2:39]OC(C)=O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:26])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]4[N:19]=[C:38]([CH3:39])[O:21][N:20]=4)=[C:16]([CH2:24][C:30]([F:36])([F:35])[F:29])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27833433,3,3-Trifluoropropionyl chlorideHCID 178423542HCID 178423542、化合物

生成物 1

HCID 866585243-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-trifluoroethyl-phenyl}-5-methyl-[1,2,4]oxadiazole収率 53%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
140 °C

実験手順

To a solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-hydroxy-2-methyl-benzamidine (i.e product of Step 1, Example 8, 400 mg, 0.93 mmol) in pyridine (10 mL) was added 3,3,3-trifluoropropionic acid chloride (0.271 g, 1.85 mmol) via syringe and the mixture was stirred at reflux for 30 min and at 140° C. in a microwave oven for 1 h. Water and EtOAc were added after cooling and the aqueous layer was extracted with EtOAc. Combined organic layers were dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel and yielded the title compound (260 mg, 53%).

後処理

  1. temperatureafter cooling
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialCombined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-9e65182763f4472a9f5ed2838566f012
出典データセット
uspto-grants-2014_01
特許番号
US08633134B2

反応ノート

読み込み中…