HCID 16117472, compound → HCID 16117473, compound

Participants

Reaction Steps

4N HCl/dioxane (3.4 mL) was added to a stirred solution of (2-{[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-carbamoyl}-ethyl)-carbamic acid t-butyl ester (1.5 g, 3.4 mmol) in CH2Cl2 (50 mL) and DMF (25 mL). The mixture was stirred at room temperature for 7 days. The mixture was filtered to give 3-amino-N-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-propionamide hydrochloride (1.0 g, 74%) as a white solid: mp 249-251° C.; 1H NMR (DMSO-d6) δ 2.00-2.04 (m, 1H), 2.37-2.65 (m, 4H, 2CH2), 2.86-2.99 (m, 3H), 4.34-4.57 (m, 4H, 2CH2), 5.11-5.18 (dd, J=4.8 and 13.1 Hz, 1H, CH), 7.46-7.64 (m, 3H, Ar), 8.02 (s, 3H, NH3), 8.78 (t, J=5.3 Hz, 1H, NH), 11.01 (s, 1H, NH); 13C NMR (DMSO-d6) δ 22.57, 31.17, 31.94, 35.09, 39.02, 46.21, 51.57, 121.71, 128.27, 130.81, 131.65, 134.28, 140.14, 167.99, 169.47, 170.96, 172.83; Anal. calcd. for C17H21N4O4Cl: C, 52.38; H, 5.69; N, 14.37; Cl, 9.09. Found: C, 52.31; H, 5.56; N, 14.19; Cl, 9.01.

Provenance & Evidence