4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid → N-methyl-N-(3-{5-[4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)glycine

Participants

Reaction Steps

Tert-butyl N-methyl-N-(3-{5-[4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)glycinate was prepared following the general procedure 7 starting from Intermediate 21 and Intermediate 4. It was hydrolyzed following procedure 8, affording the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.50-8.37 (m, 2H), 8.32 (br s, 1H), 8.21 (d, J=7.4 Hz, 1H), 7.88 (d, J=8.6 Hz, 1H), 7.82-7.67 (m, 2H), 4.47 (s, 2H), 4.09 (s, 2H), 3.18 (m, 1H), 3.03-2.91 (m, 1H), 2.80 (s, 3H), 2.69-2.57 (m, 1H). 1.89-1.16 (m, 6H), 0.79 (d, J=6.1 Hz, 3H). LC/MS (Method B): 487.4 (M−H)−, 489.4 (M+H)+. HPLC (Method A) Rt 5.10 min (Purity: 100%).

Provenance & Evidence