Water → HCID 10174262, compound

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 rac-2-(methylamino)-1-thien-2-ylethanol (Preparation 46, 0.130 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; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.125 g of the title compound as a white solid. Physical characteristics. M.p. 145-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 7.41-7.32, 6.97-6.93, 6.87, 6.42, 5.52, 4.984.93, 4.55, 3.91, 3.76, 2.70-2.60, 2.30; 13C NMR (100 MHz, CDCl3) δ 168.9, 159.9, 148.3, 145.6, 140.3, 136.2, 132.4, 127.9, 124.1, 123.8, 121.8, 119.8, 119.0, 112.0, 109.9, 101.8, 61.3, 59.6, 49.2, 37.7, 37.0, 32.9; MS (ESI+) m/z 486 (M+H)+.

Provenance & Evidence