3-{Ethyl[1-(propan-2-yl)piperidin-4-yl]amino}-2-methyl-5-(trifluoromethyl)benzoic acid → 5-chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-2-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)benzamide formate

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Methyl 5-chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-2-methylbenzoate was hydrolyzed to 5-chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-2-methylbenzoic acid following the same preparation method for 3-{Ethyl[1-(propan-2-yl)piperidin-4-yl]amino}-2-methyl-5-(trifluoromethyl)benzoic acid from its corresponding carboxylate. The crude 5-chloro-3-(ethyl(1-methylazetidin-3-yl)amino)-2-methylbenzoic acid was then coupled with 3-(Aminomethyl)-6-methyl-4-propyl-1,2-dihydropyridin-2-one HCl salt prepared earlier following the preparation method described for N-[(4,6-Dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-3-[ethyl(1-methylpiperidin-4-yl)amino]-2-methyl-5-(trifluoromethyl)benzamide. After purification by reverse phase HPLC/MS (CAN-H2O containing 0.1% formic acid), the titled compound was obtained. 1H-NMR (500 MHz, CD3OD) δ ppm 8.58-8.24 (br, 1H), 7.15 (d, J=2.0 Hz, 1H), 7.08 (d, J=2.0 Hz, 1H), 6.14 (s, 1H), 4.48 (s, 2H), 4.41-4.34 (m, 1H), 4.25 (br, 2H), 3.85 (br, 2H), 3.00 (q, J=7.0 Hz, 2H), 2.92 (s, 3H), 2.72-2.66 (m, 2H), 2.34 (s, 3H), 2.26 (s, 3H), 1.70-1.61 (m, 2H), 1.04 (t, J=7.2 Hz, 3H), 0.91 (t, J=7.0 Hz, 3H); MS (ES) (M+H) 445.48.

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