3-(Methoxymethyl)-4-(2-methylpiperidin-1-yl)benzoic acid → tert-butyl N-(2-fluoro-5-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate

Participants

Reaction Steps

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 60 (256.87 mg; 0.83 mmol) and Intermediate 58 (197.50 mg; 0.75 mmol). The reaction mixture was filtered through a SPE NH2 column (10 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1), affording the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.31 (d, J=2.1 Hz, 1H), 8.22 (dd, J=7.0, 2.2 Hz, 1H), 8.11-8.06 (m, 2H), 7.23-7.14 (m, 2H), 4.67-4.55 (m, 2H), 4.16-4.08 (m, 2H), 3.89 (s, 2H), 3.49 (s, 3H), 3.27 (s, 2H), 3.18-3.12 (m, 1H), 3.06-2.99 (m, 1H), 2.67-2.59 (m, 1H), 2.46 (s, 3H), 1.89-1.76 (m, 2H), 1.73-1.65 (m, 2H), 1.51 (s, 9H), 0.89 (d, J=6.3 Hz, 3H). LC/MS (Method B): 539.4 (M+H)+. HPLC (Method A) Rt 3.84 min (Purity: 99.1%).

Provenance & Evidence