Reaction Steps
A mixture of 4-aminomethyl-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione hydrochloride (0.50 g, 1.6 mmol), 1-naphthyl isocyanate (0.26 g, 1.6 mmol), and diisopropylethylamine (0.40 g, 3.1 mmol) in 10 mL pyridine was warmed to 40° C. with stirring under N2, and the resulting solution was stirred at the same temperature for 2 hours. The mixture was cooled, and the solvent was evaporated under vacuum. The residue was chromatographed, eluting with 95:5 methylene chloride-methanol, to provide 0.40 g of the product in 60% yield: mp 250-252° C.; 1H NMR (DMSO-d6) δ 2.06-2.11 (m, 1H), 2.51-2.65 (m, 2H), 2.85-2.97 (m, 1H), 4.78 (d, J=6.0 Hz, 2H), 5.18 (dd, J=12.6 Hz, d=5.4 Hz, 1H), 7.23 (t, J=6.0, 1H), 7.41 (t, J=7.9 Hz, 1H), 7.49-7.58 (m, 3H), 7.80-7.91 (m, 4H), 7.98 (d, J=7.3, 1H), 8.12 (d, J=7.6 Hz, 1H), 8.81 (s, 1H), 11.20 (s, 1H); 13C NMR (DMSO-d6) δ 22.0, 31.0, 38.9, 48.9, 116.8, 121.4, 121.9, 122.3, 125.4, 125.7, 125.8, 125.9, 127.3, 128.3, 131.7, 133.7, 133.8, 134.8, 134.9, 140.2, 155.7, 167.0, 167.6, 169.8, 172.8; Anal. calcd. for C25H20N4O5.0.25H2O: C, 65.14; H, 4.48; N, 12.15. Found: C, 65.08; H, 4.48; N, 11.96.
