Benzoic Acid → N-{6-[3-(benzylamino)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (20.0 mg, 0.065 mmol), benzoic acid (16.5 mg, 0.135 mmol), HATU (42.3 mg, 0.111 mmol), N,N-diisopropylethylamine (35.0 μL, 0.204 mmol) and pyridine (1.5 mL) was stirred at 60° C. for 4 hr. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, the residue was dissolved in tetrahydrofuran (1.0 mL), and the mixture was stirred at room temperature. A solution (2.0 mL, 2.0 mmol) of 1M borane-tetrahydrofuran-complex/tetrahydrofuran was added thereto, and the mixture was stirred at room temperature for 39 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (7.7 mg, 30%).

Herkunft & Nachweise