Toluene → 6-(Difluoro(6-(1-methyl-1H-pyrazol-4-yl)-1,2,4-triazolo(4,3-b)pyridazin-3-yl)methyl)quinoline

Participants

Reaction Conditions

Reaction Steps

The crude 6-{1,1-difluoro-2-[(6E)-6-hydrazono-3-(1-methyl-1H-pyrazol-4-yl)pyridazin-1(6H)-yl]-2-oxoethyl}quinoline from step 3 above (3.67 mmol) was brought in a reaction balloon under argon. 36 mL of 1-methoxy-2-propanol was added and the mixture was stirred at 105° C. for 1 h. Then the reaction mixture was brought to gentle reflux for one additional hour (108° C.). The reaction mixture was allowed to cool to room temperature and poured out in a solution of 10 g of sodium carbonate in 100 mL of water. 100 mL toluene was added and the layers were separated. The water layer was extracted with toluene (100 mL). The combined organic layers were washed with water and evaporated, yielding 700 mg of compound (I) (1.86 mmol; 51%).

Provenance & Evidence