Water → n-(4-Chlorobenzyl)-2-(((2-(3-furyl)-2-hydroxyethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

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 rac-1-(3-furyl)-2-(methylamino)ethanol (Preparation 43, 0.116 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 and was poured into water (25 mL). The suspension was filtered and the resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2) followed by recrystallization from ethyl acetate to yield 0.102 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 93-97° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.55, 7.54-7.53, 7.41-7.32, 6.87, 6.42, 4.97, 4.694.65, 4.55, 3.91, 3.74, 2.63-2.53, 2.30; 13C NMR (100 MHz, CDCl3) δ 173.7, 164.7, 153.2, 150.6, 143.4, 141.1, 139.4, 137.3, 132.8, 128.9, 126.0, 116.8, 114.7, 108.3, 106.6, 102.1, 63.2, 62.7, 54.1, 42.6, 41.8, 37.8; MS (ESI+) m/z 470 (M+H)+.

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