Dimethylamine → HCID 58827242, compound

Participants

Reaction Steps

To a stirred solution of [2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylamino]acetic acid (0.73 g, 2.2 mmol) in DMF (20 mL), were successively added HOBt (0.32 g, 2.4 mmol), DBU (0.38 g, 2.5 mmol), dimethylamine (90 mg, 2 mmol) and EDC-Cl (0.58 g, 3.0 mmol). The solution was stirred overnight at room temperature. The solvent was evaporated in vacuo, giving a yellow oil. The oil was dissolved in CH2Cl2 (200 mL), washed with water (3×100 mL) and brine (100 mL), and dried (MgSO4). The solvent was evaporated in vacuo to give a yellow solid. Following an ethanol trituration, the resulting solid was purified by preparative HPLC, giving 0.52 g of the product in 73% yield: mp 239-241° C.; 1H NMR (DMSO-d6) δ 2.02-2.06 (m, 1H), 2.47-2.63 (m, 2H), 2.83-3.01 (m, 7H), 4.15 (d, J=3.9 Hz, 2H), 5.08 (dd, J=12.6 Hz, J=5.3 Hz, 1H), 7.05-7.10 (m, 3H), 7.60 (t, J=8.1 Hz, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6) δ 22.12, 30.96, 35.04, 35.34, 45.53, 48.55, 109.48, 110.72, 118.13, 131.98, 136.12, 145.36, 167.31, 167.59, 168.75, 170.02, 172.76; Anal. calcd. for C17H18N4O5.0.3H2O: C, 56.13; H, 5.15; N, 15.40. Found: C, 56.17; H, 5.15; N, 15.26.

Provenance & Evidence