Reaction #595357

Reaction equation

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

Solvents

acetonitrile

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe organic phase is washed with saturated sodium chloride solution
3. 3
   Dryingdried over sodium sulfate
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue is purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5)

Procedure

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.

Source