Sodium Chloride → HCID 10152976, compound

Participants

Reaction Steps

A mixture of N-(4-chlorobenzyl)-2-(((3-chloro-2-hydroxypropyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 63, 0.181 g), 2-methoxythiophenol (0.058 mL), and diisopropylethylamine (0.097 mL) in absolute EtOH (16 mL) was heated to reflux overnight. The reaction was poured into 50% saturated aqueous NaCl (50 mL) and extracted with CHCl3. The combined organic layers were dried and concentrated. The crude product was purified by column chromatography (acetone/CHCl3/NH4OH; 1/2/0.5%) and triturated with Et2O/hexanes. The resulting solid was collected and dried overnight to yield 0.10 g of the title compound as a white solid. Physical characteristics. M.p. 145-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.66, 8.52, 7.40, 7.34, 7.22, 7.13, 6.89, 4.96, 4.55, 3.84-3.64, 3.02, 2.84, 2.55, 2.44, 2.29; 13C NMR (DMSO-d6) δ 174.1, 165.7, 157.4, 154.5, 152.7, 143.1, 140.0, 132.8, 130.5, 129.8, 128.1, 127.4, 126.8, 122.3, 116.6, 115.2, 112.0, 107.2, 68.8, 62.1, 56.9, 55.0, 44.3, 42.7, 38.8, 37.5. Anal. Found: C, 60.38; H, 5.56; N, 7.45.

Provenance & Evidence