Potassium Carbonate → 7-(4-chlorophenyl)-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (1.1 g, 3.4 mmol), prepared as described in Example 244, K2CO3 (940 mg, 6.8 mmol), and 5-chloromethyl-2-trifluoromethylpyridine (800 mg, 4.1 mmol) in DMF (8.3 mL) was heated at 65° C. for 40 min. After this time, the solution was cooled to RT The reaction mixture was partitioned between water and EtOAc. The organic layer separated, washed with water and saturated aqueous NaCl. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with hexanes/EtOAc to give the title compound, 7-(4-chlorophenyl)-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (1.25 g, 76%) as a yellow solid. HPLC: 2.84 min; MS, M+H=483; 1H NMR (CDCl3) δ 8.80 (d, J=1.4 Hz, 1H), 8.65 (Abq, J=1.6, 4.4 Hz, 2H), 8.23 (s, 1H), 7.96 (m, 1H), 7.68 (d, J=8.3 Hz, 1H), 7.34 (m, 2H), 7.23 (m, 2H), 7.10 (m, 2H), 5.31 (2H).

Provenance & Evidence