Sodium Hydroxide → [4-(6-Phenethylsulfanylpyridazin-3-YL)piperazin-1-YL](2-trifluoromethylphenyl)methanone

HRID 1684997ノート

反応式

HRID 1684997 の反応式
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:26]1([CH2:32][CH2:33][SH:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH-].[Na+]>O1CCOCC1.O>[CH2:33]([S:34][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)[CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 781262-PhenylethanethiolHCID 86024941[4-(6-Chloropyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone

生成物 1

HCID 11155686[4-(6-Phenethylsulfanylpyridazin-3-YL)piperazin-1-YL](2-trifluoromethylphenyl)methanone収率 44.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

A mixture of [4-(6-chloro pyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (0.089 g, 0.240 mmol), 2-phenylethanethiol (0.049 g, 0.36 mmol) and sodium hydroxide (9.6 mg) in 5 mL 1,4-dioxane was heated at 100-110° C. overnight. The reaction mixture was cooled to room temperature, diluted with 20 mL of water, and then extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulphate, then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid (50 mg, 43.7% yield). 1H NMR (400 MHz, CDCl3) δ 7.65, 7.52-7.55, 7.47-7.48, 7.27, 7.12-7.22, 7.03, 6.76, 3.89-3.94, 3.79-3.84, 3.54-3.61, 3.49-3.51, 3.45, 3.17-3.25, 2.97.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-13d83b58646d4c38b818a876f4634c89
出典データセット
uspto-grants-2012_04
特許番号
US08148378B2

反応ノート

読み込み中…