3-Pyridinecarbonyl chloride, hydrochloride (1:1) → N-[5-(2-benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]nicotinamide

Participants

Reaction Conditions

Reaction Steps

To a solution of [5-(2-benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.52 g, 1.4 mmol) and 4-dimethylaminopyridine (0.051 g, 0.42 mmol) in N,N-dimethylacetamide (10 mL) was added nicotinoyl chloride hydrochloride (0.37 g, 2.1 mmol), and the mixture was stirred at 80° C. for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The resulting crystals were crystallized from isopropyl ether to give the title compound (0.28 g, yield 59%).

Provenance & Evidence