1-Hydroxybenzotriazole → 6-[4-(6-Bromopyridine-3-carbonyl)piperazin-1-yl]-5-methylnicotinonitrile

Participants

Reaction Steps

6-Bromonicotinic acid (500 mg), 1-(3,5-dimethylpyridin-2-yl)piperazine (501 mg) described in Preparation Example 79, 1-hydroxybenzotriazole 1 hydrate (379 mg) and triethylamine (0.69 mL) were dissolved in N,N-dimethylformamide (10 mL), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (569 mg) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 5% aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (709 mg).

Provenance & Evidence