Diisopropylethylamine → HCID 178522482, compound

Participants

Reaction Steps

A mixture of 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid (2.5 g), HBTU (4.41 g) and DIEA (4.0 mL) in DMF (20 mL) were stirred at room temperature for 10 minutes. To this reaction mixture was added 5-(3-chloro-5-fluoro-phenyl)-1H-benzoimidazol-2-ylamine hydrobromide salt (3.46 g), and the mixture was heated at 80° C. for 30 minutes. After cooling the reaction mixture to room temperature, an aqueous sodium bicarbonate solution (200 mL) was added, and the mixture was stirred for 30 minutes. The mixture was then filtered, washed with water, dried, and purified on a 80 g pre-packaged silica gel column with a gradient of 0 to 10% 2 M ammonia-methanol in DCM. 4.4 g of 6-chloro-imidazo[1,2-b]pyridazine-2-carboxylic acid [5-(3-chloro-5-fluoro-phenyl)-1H-benzoimidazol-2-yl]-amide was obtained. LCMS (m/z): 441.9. 1H NMR (400 MHz, DMSO-d6) δ 12.18 (2H, br. s.) 9.08 (1H, s) 8.32-8.39 (1H, m) 7.82 (1H, s) 7.46-7.64 (6H, m).

Provenance & Evidence