1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-fluoro-N-[4-(imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-5-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To the solution of 4-(imidazo[1,2-b]pyridazin-6-ylethynyl)aniline (93.6 mg, 0.4 mmol, 1 eq) and 2-fluoro-4-methylbenzoic acid (62.3 mg, 1 eq) in anhydrous dichloroethane (3 mL) under nitrogen atmosphere at room temperature was added 4-(dimethylamino)pyridine (10 mg, 0.2 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (92.2 mg, 1.2 eq). After the reaction was stirred at 60° C. for 3 hours, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the solid residue was triturated with EtOAc-Hex (2:1) to yield 2-fluoro-N-[4-(imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-5-methylbenzamide as a slightly yellow solid in amount of 122 mg.

Provenance & Evidence