Potassium Carbonate → HCID 59716722, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of 8-chloro-7-p-tolyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (2.2 g, 8.4 mmol) and 5-(chloromethyl)-2-(trifluoromethyl)pyridine (2.1 g, 11 mmol) in DMF (15 mL) at room temperature under argon was added K2CO3 (1.74 g, 12.6 mmol). The resulting mixture was heated at 55° C. for 2 h. HPLC/MS analysis indicated complete reaction. The reaction mixture was concentrated under vacuum with co-evaporation of toluene (10 mL×2) to obtain a dark yellow solid. The crude product was purified by silica gel column chromatography (ISCO) eluting with hexanes/EtOAc/CH2Cl2. Desired product (2.1 g) was obtained as a brown solid. Washing with MeOH (10 mL×2) and drying provided pure title compound, 8-chloro-7-p-tolyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (1.76 g, 56%) as a light yellow solid. MS [M+H]+ 420; HPLC retention time=3.53 min; 1HNMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.13 (s, 1H), 8.00 (d, 1H), 7.70 (d, 1H), 7.30-7.50 (m, 4H), 5.36 (s, 2H), 2.45 (s, 3H).

Provenance & Evidence