N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenyl-1-butyn-1-yl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide → N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenylbutyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

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Reaction Steps

N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenylbut-1-ynyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 88, 0.200 g) was dissolved in ethanol (60 mL) with heating and then allowed to cool to room temperature. The mixture was hydrogenated over 10% Pd/C (0.060 g) at 35 psi for 1.5 h. The reaction mixture was filtered through a Celite pad and the pad was washed with CH2Cl2 (60 mL). The filtrate was concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.008 g of the title compound as a yellow solid. Physical characteristics. 1H NMR (400 MHz, DMSO-d6) δ 10.68, 8.51, 7.40-7.30, 6.64, 5.20, 4.584.53, 4.54, 3.90, 2.75-2.72, 1.76-1.64; MS (ESI+) m/z 465 (M+H)+.

Provenance & Evidence