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

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Reaction Conditions

Reaction Steps

Ethyl chloroformate (150.1 ml) was added to a suspension of N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 1, 262.0 g) and CH2Cl2 with very low water content (2.63 L). The slurry was warmed to 39-40° C. After 2 h, the reaction mixture was cooled to room temperature and ethyl ether (2.63 L) was added. The mixture was stirred overnight, filtered, was washed with ethyl ether (3×2 L), and dried in a vacuum oven (40° C.) to afford 221.8 g of the title compound as a colorless solid. Physical characteristics. 1H NMR (400 MHz, TFA-d) δ 11.50, 8.94, 7.23, 4.64, 4.27; 13C NMR (100 MHz, TFA-d) δ 167.3, 165.2, 155.8, 155.1, 140.4, 134.2, 132.7, 128.4, 128.3, 113.5, 110.6, 103.8, 43.4, 38.9, 33.8. Anal. Found: C, 55.89; H, 3.69; N, 7.60; Cl, 18.98.

Provenance & Evidence