Reaction #595358

Reaction equation

compound

2-Amino-4-[4-(2-hydroxyethoxy)phenyl]-6-mercaptopyridine-3,5-dicarbonitrile

compound

4-(Chloromethyl)-2-(4-chloro-3-methylphenyl)-1,3-oxazole

sodium bicarbonate

→

2-Amino-6-({[2-(4-chloro-3-methylphenyl)-1,3-oxazol-4-yl]methyl}thio)-4-[4-(2-hydroxyethoxy)-phenyl]pyridine-3,5-dicarbonitrile

Solvents

DMF

Conditions

Workup

1. 1
   FiltrationThe mixture is then filtered
2. 2
   Otherthe filtrate is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
3. 3
   OtherAfter removal of the solvent
4. 4
   Otheron a rotary evaporator
5. 5
   Otherthe product is obtained as a white solid

Procedure

52 mg (0.17 mmol) of the compound from Example 1A and 89 mg (0.18 mmol) of the compound from Example 28A, together with 42 mg (0.50 mmol) of sodium bicarbonate, are suspended in 1.8 ml of dry DMF. The reaction mixture is stirred at RT for 12 h. The mixture is then filtered and the filtrate is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). After removal of the solvent on a rotary evaporator, the product is obtained as a white solid.

Source