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

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Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (0.11 mL) and 2-(methylamino)-1-pyridin-3-ylethanol (Preparation 39, 0.094 g) were added to a suspension of N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 2, 0.150 g) in DMF (10 mL). The reaction mixture was heated to 90° C. for 1 h. The mixture was allowed to cool to room temperature, poured into water (25 mL), and was extracted with CH2Cl2 (4×25 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 98/2, 97/3, 96/4, 95/5) followed by recrystallization from ethyl acetate to yield 0.074 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 145-149° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.64, 8.54, 8.50, 8.40-8.39, 7.69-7.67, 7.41-7.33, 7.29-7.25, 6.83, 5.33, 4.77-4.73, 4.55, 3.88, 3.71, 2.67-2.55, 2.32; MS (ESI+) m/z 481 (M+H)+.

Provenance & Evidence