Water → HCID 10288846, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Diisopropylethylamine (0.11 mL) and rac-2-methylamino)-1-pyridin-2-ylethanol (Preparation 36, 0.094 g) were added to a suspension of N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide (Example 2, 0.150 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 was extracted with CH2Cl2 (4×25 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2, 97/3, 95/5) followed by recrystallization from ethyl acetate to yield 0.082 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 130-132° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 8.43-8.42, 7.76-7.73, 7.47-7.45, 7.41-7.32, 7.24-7.21, 6.83, 5.31, 4.79-4.74, 4.55, 3.89, 3.74, 2.79-2.74, 2.66-2.61, 2.33; MS (ESI+) m/z 481 (M+H)+. Anal. Found: C, 62.08; H, 5.25; N, 11.57; Cl, 7.39.

Provenance & Evidence