Water → N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-(3-methoxyphenyl)-ethyl)(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 1-(3-methoxyphenyl)-2-(methylamino)ethanol (Preparation 31, 0.112 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 0.102 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 116-120° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 7.41-7.32, 7.18, 6.88-6.85, 6.77-6.75, 5.10, 4.704.66, 4.55, 3.89, 3.74, 3.70, 2.61, 2.33; MS (ESI+) m/z 510 (M+H)+. Anal. Found: C, 63.48; H, 5.56; N, 8.24; Cl, 6.94.

Provenance & Evidence