3-(Methoxymethyl)-4-(2-methylpiperidin-1-yl)benzoic acid → N-(2-fluoro-4-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}benzoyl)-beta-alanine

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Ethyl N-(2-fluoro-4-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}benzoyl)-beta-alaninate was prepared following the general procedure 3 starting from Intermediate 2 and Intermediate 6. It was hydrolyzed following general procedure 9 to afford the title compound as a pale yellow powder. 1H NMR (DMSO-d6, 300 MHz) δ 12.3 (brs, 1H), 8.56 (m, 1H), 8.18 (m, 1H), 8.06 (m, 1H), 7.97 (m, 1H), 7.90 (dd, J=8.0 Hz, 1H), 7.81 (t, 1H, J=7.6 Hz), 7.38 (d, J=8.5 Hz, 1H), 4.54 (m, 2H), 3.47 (m, 2H), 3.40 (s, 3H), 3.23 (m, 1H), 3.02 (m, 1H), 2.56-2.47 (m, 3H), 1.88-1.30 (m, 7H), 0.85 (d, J=6.2 Hz, 3H). LC/MS (Method B): 497.4 (M+H)1, 495.4 (M−H)−. HPLC (Method A) Rt 3.01 min (Purity: 97.2%).

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