HCID 22498763, compound → HCID 22498716, compound

Participants

Reaction Steps

N-(4-Chlorobenzyl)-2-(5-hydroxypent-1-ynyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 84, 0.125 g) was dissolved in ethanol (40 mL) with heating and then allowed to cool to room temperature. The mixture was hydrogenated over 10% Pd/C (0.038 g) at 35 psi for 2 h. The reaction mixture was filtered through a Celite pad and the pad was washed with CH2Cl2 (75 mL). The filtrate was concentrated in vacuo and then resubjected to the reaction conditions for 1 h. The resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2) followed by recrystallization from ethyl acetate to yield 0.061 g of the title compound as a white solid. Physical characteristics. M.p. 151-152° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.69, 8.51, 7.41-7.32, 6.67, 4.54, 4.37, 3.92, 3.41-3.37, 2.73, 1.68-1.63, 1.49-1.42, 1.40-1.33; MS (ESI+) m/z 403 (M+H)+.

Provenance & Evidence