Diisopropylethylamine → HCID 70873923, compound

Participants

Reaction Steps

To a stirred solution of (3-[benzyl(ethyl)amino]-2-methylbenzoic acid (91% purity, 296 mg, 1.0 mmol) in DMF (10 ml) was added DIPEA (440 μl, 2.5 mmol) and HATU (570 mg, 1.5 mmol). The reaction was stirred at room temperature for 5 min after which time 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (89%, 222 mg, 1.3 mmol) was added and the reaction was stirred at room temperature for 16 h. The reaction mixture was then poured onto 150 ml of water and stirred for 20 min. The product was filtered, air dried under vacuum and then purified using RP-HPLC. The resulting solid was triturated with diethyl ether and isolated by filtration to afford the title compound as an off white solid (86 mg, 21%). LC-MS 99%, m/z=404.3, 1H NMR (500 MHz, Chloroform-d) δ 12.04 (s, 1H), 7.33-7.23 (m, 4H), 7.21 (t, J=6.8 Hz, 1H), 7.14-7.05 (m, 3H), 7.05-6.99 (m, 1H), 5.92 (s, 1H), 4.53 (d, J=5.9 Hz, 2H), 4.06 (s, 2H), 2.92 (q, J=6.9 Hz, 2H), 2.41 (s, 3H), 2.39 (s, 3H), 2.16 (s, 3H), 0.92 (t, J=7.0 Hz, 3H).

Provenance & Evidence