Water → N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-phenylethyl)(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 (0.111 mL) and (x-(methylaminomethyl)-benzyl alcohol (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 and was poured into water (25 mL). The suspension was filtered and the resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.095 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 118-121° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 7.41-7.35, 7.32-7.25, 7.22-7.18, 6.84, 5.10, 4.734.69, 4.55, 3.89, 3.73, 2.62-2.54, 2.32; MS (ESI+) m/z 480 (M+H)+. Anal. Found: C, 63.48; H, 5.56; N, 8.24; Cl, 6.94.

Provenance & Evidence