Reaction Steps
A mixture of 2-azido-N-[2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-acetamide (1.4 g, 3.8 mmol) and 10% Pd/C (0.2 g) in methanol (100 mL) and 4N HCl (20 mL) was hydrogenated in Parr Shaker for 5 hours. H2O (10 mL) was added, and the mixture was filtered through celite. The filtrate was concentrated, and the residue was evaporated with ethanol (3×20 mL). The solid was slurried with hot methanol (30 mL) to give 2-amino-N-[2-(3-methyl-2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-acetamide hydrochloride (0.5 g, 35%) as a yellow solid: mp 111-113° C.; 1H NMR (DMSO-d6) δ 1.90 (s, 3H, CH3), 2.04-2.09 (m, 1H), 2.50-2.72 (m, 3H), 3.97 (s, 2H, CH2), 7.64 (d, J=7.2 Hz, 1H, Ar), 7.86 (t, J=7.7 Hz, 1H, Ar), 8.32 (d, J=8.2 Hz, 1H, Ar), 8.40 (s, 3H, NH3), 10.30 (s, 1H, NH), 11.05 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.05, 28.55, 29.10, 41.11, 58.83, 117.98, 118.92, 127.13, 131.76, 134.74, 135.99, 166.18, 167.22, 167.75, 172.04, 172.18; Anal. calcd. for C16H17N4O5Cl: C, 50.47; H, 4.50; N, 14.71; Cl, 9.31. Found: C, 50.35; H, 4.40; N, 14.54; Cl, 9.01.
