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

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (0.14 mL) and N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 2, 0.150 g) were added to a solution of synephrine (0.137 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, poured into water (25 mL), and extracted with CH2Cl2 (4×25 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The resulting oil was purified by column chromatography (CH2Cl2/methanol; 98/2, 97/3) followed by recrystallization from ethyl acetate/methanol to yield 0.120 g of the title compound as a white solid. Physical characteristics. M.p. 117-122° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 9.21, 8.54, 7.41-7.33, 7.09, 6.85, 6.65, 4.88, 4.614.57, 4.55, 3.89, 3.71, 2.58-2.45, 2.30; 13C NMR (100 MHz, CDCl3) δ 173.7, 164.8, 156.1, 153.2, 150.9, 141.2, 137.1, 132.9, 132.8, 128.9, 128.7, 127.4, 116.6, 115.3, 114.8, 106.6, 69.5, 64.0, 54.0, 42.6, 42.2, 37.8; MS (ESI+) m/z 496 (M+H)+

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