Diisopropylethylamine → 5-Chloro-3-[ethyl(1-methylpiperidin-4-yl)amino]-2-methyl-N-{[6-methyl-2-oxo-4-(propan-2-yl)-1,2-dihydropyridin-3-yl]methyl}benzamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-chloro-3-[ethyl(1-methylpiperidin-4-yl)amino]-2-methylbenzoic acid (crude material, ˜0.7 mmol) and 3-(aminomethyl)-6-methyl-4-(propan-2-yl)-1,2-dihydropyridin-2-one hydrochloride HCl salt (200 mg, 0.91 mmol) in DMSO (5.3 mL) was added PyBOP (550 mg, 1.05 mmol) and hunig base (366 ul, 2.10 mmol). The reaction mixture was stirred at 23° C. for 7 hours. The reaction mixture was quenched with water and resulting precipitate was collected. The solid was purified by silica gel column chromatography (NH—SiO2 Ethylacetate/MeOH=10/1+10% triethylamine). The crude compound was triturated from ethylacetate/hexane, and dried to give the titled compound as a white solid (166 mg, 50% yield). 1H-NMR (400 MHz, CDCl3) δppm; 7.06 (d, J=2.4 Hz, 1H), 7.01-7.05 (m, 1H), 7.00 (d, J=2.4 Hz, 1H), 6.04 (s, 1H), 4.57 (d, J=6.0 Hz, 2H), 3.49-3.57 (m, 1H), 3.02 (q, J=6.8 Hz, 2H), 2.80-2.84 (m, 2H), 2.61-2.69 (m, 1H), 2.29 (s, 3H), 2.23 (s, 3H), 2.23 (s, 3H), 1.86-1.90 (m, 2H), 1.66-1.70 (m, 4H), 1.21 (d, J=6.8 Hz, 6H), 0.84 (t, J=6.8 Hz, 3H); MS (ES) [M+Na] 495.2; HPLC 95.7% purity.

Provenance & Evidence