Reaktion #2456393

Reaktionsgleichung

2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(methyl-thio)pyridine-3,5-dicarbonitrile

4-hydroxypiperidine

ammonium chloride

ethyl acetate

→

title compound

2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(4-hydroxypiperidin-1-yl)pyridine-3,5-dicarbonitrile

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 8 h
2. 2
   SonstigeAfter vigorous mixing, the organic phase is separated off
3. 3
   Waschenwashed with saturated sodium chloride solution
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered off
6. 6
   Sonstigethe solvent is removed on a rotary evaporator
7. 7
   SonstigeThe residue is purified initially by column chromatography on silica gel 60 (mobile phase: gradient toluene/ethyl acetate 3:1→1:1)

Vorschrift

100 mg (0.23 mmol) of 2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-4-(methyl-thio)pyridine-3,5-dicarbonitrile and 1000 mg (9.89 mmol) of 4-hydroxypiperidine are combined in 2 ml of acetone and stirred under reflux for 8 h. The mixture is then added to a mixture of semiconcentrated aqueous ammonium chloride solution and ethyl acetate. After vigorous mixing, the organic phase is separated off, washed with saturated sodium chloride solution, dried over magnesium sulfate and filtered off using a glass frit, and the solvent is removed on a rotary evaporator. The residue is purified initially by column chromatography on silica gel 60 (mobile phase: gradient toluene/ethyl acetate 3:1→1:1) and then by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). The title compound in obtained as a white powder.

Quelle