Potassium Carbonate → 6-(4-(2,4-Difluorophenyl)-1-methyl-1H-imidazol-5-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine

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Reaction Conditions

Reaction Steps

N-((3-Isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)methylene)methanamine (0.154 g, 0.758 mmol; Preparation #AP.1.1) and 2,4-difluoro-1-(isocyano(tosyl)methyl)benzene (0.233 g, 0.758 mmol, J. W. Pharmlab) were added to a 25 mL flask in DMF (4 mL). To the mixture was added K2CO3 (0.105 g, 0.758 mmol) and the mixture was heated to about 60° C. for about 17 h. The solvent was removed in vacuo and the material was washed with saturated aqueous NaHCO3 (10 mL) and extracted with EtOAc (15 mL), dried over MgSO4, filtered and concentrated to dryness. The residue was purified by flash chromatography (using MeOH/DCM 0-5% gradient) and then triturated with Et2O and dried in a vacuum oven overnight to afford the title compound as an off-white solid (0.062 g, 23%): LC/MS (Table 1, Method g) Rt=2.03 min; MS m/z: 355.2 (M+1)+.

Provenance & Evidence