反応 #595357

反応方程式

2-amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-[3-fluoro-4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile

isoamyl nitrite

ammonium chloride

→

2-Chloro-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-[3-fluoro-4-(2-hydroxy-ethoxy)phenyl]pyridine-3,5-dicarbonitrile

溶媒

acetonitrile

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   洗浄The organic phase is washed with saturated sodium chloride solution
3. 3
   乾燥dried over sodium sulfate
4. 4
   濃縮concentrated
5. 5
   その他The residue is purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5)

実験手順

150 mg (0.287 mmol) of 2-amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-[3-fluoro-4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile (Example 20) are initially charged in 20 ml of acetonitrile, 258 μl (1.724 mmol) of isoamyl nitrite and 232 mg (1.724 mmol) of copper(II) chloride are added and the mixture is stirred at room temperature overnight. The reaction mixture is then added to saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The residue is purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5). This gives 25 mg (16% of theory) of the target compound.

出典