Water → N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-(5-phenyl-2-furyl)ethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (0.17 mL) was added to a solution of N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 2, 0.183 g) and rac-2-(methylamino)-1-(5-phenyl-2-furyl)ethanol (Preparation 55, 0.217 g) in DMF (15 mL). The reaction mixture was heated to 90° C. for 2 h. The mixture was allowed to cool to room temperature, poured into water (50 mL), and was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by column chromatography (CH2Cl2/methanol, 100/1; 50/1; 25/1) and crystallized from ethyl acetate/CH2Cl2/diethyl ether to afford 0.22 g of the title compound as a white solid. Physical characteristics. M.p. 115-119°C.; 1H NMR (400 MHz, DMSO-d6) δ 10.63, 8.40, 7.56, 7.42-7.30, 7.17, 6.89, 6.84, 6.37, 5.34, 4.74, 4.54, 3.80, 3.74, 3.67, 2.88, 2.68, 2.33; MS (ESI+) m/z 546 (M+H)+.

Provenance & Evidence