Water → HCID 10238911, 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-(1-methyl-1H-pyrrol-2-yl)ethanol (Preparation 48, 0.126 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 oil was purified by column chromatography (CH2Cl2/methanol, 98/2) followed by recrystallization from ethyl acetate to yield 0.126 g the title compound as a white solid. Physical characteristics. M.p. 122-124° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.55, 7.41-7.32, 6.89, 6.61-6.60, 5.85-5.83, 4.84, 4.74-4.69, 4.55, 3.91, 3.79-3.71, 3.58, 2.79-2.70, 2.31; 13C NMR (100 MHz, CDCl3) δ 173.7, 164.7, 153.2, 150.6, 141.1, 137.3, 132.8, 131.4, 128.9, 128.6, 123.4, 116.8, 114.8, 106.8, 106.6, 106.0, 61.9, 60.8, 54.3, 42.5, 41.9, 37.8, 34.1; MS (ESI+) m/z 483 (M+H)+.

Provenance & Evidence