Réaction #1247413

Équation de réaction

7-(4-chlorophenyl)-2-methyl-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione

4-(bromomethyl)benzonitrile

K2CO3

→

4-((7-(4-chlorophenyl)-2-methyl-3,6-dioxo-8-(pyridin-4-yl)-2,3-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-5(6H)-yl)methyl)benzonitrile

Rendement 49.5%

Solvants

DMF

ethyl acetate

Conditions de réaction

Traitement

1. 1
   LavageThe resulting solution was then washed with water
2. 2
   SéchageThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe crude product was purified by reverse phase HPLC

Mode opératoire

The solution of 7-(4-chlorophenyl)-2-methyl-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione (10 mg, 0.028 mmol), 4-(bromomethyl)benzonitrile (7 mg, 0.036 mmol), K2CO3(12 mg, 0.084 mmol) in DMF (0.5 ml), was heated at 80° C. for 20 min. After this time, the reaction mixture was cooled to RT and diluted with ethyl acetate. The resulting solution was then washed with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by reverse phase HPLC to give the title compound, 4-((7-(4-chlorophenyl)-2-methyl-3,6-dioxo-8-(pyridin-4-yl)-2,3-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-5(6H)-yl)methyl)benzonitrile (6.5 mg, 40%) as the mono trifluoro acetate salt as a yellow solid. Rt=2.78, M+H=469; 1H NMR (CD3OD) δ 8.81(2H), 7.71-7.60(6H), 7.32(2H), 7.07(2H), 5.96(2H), 3.57(3H).

Source