Hydrochloric Acid → HCID 71711894, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(tert-butoxy)-2-(2-methyl-6-phenethyl-4-(p-tolyl)-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)acetate (intermediate 19) (34.1 mg, 0.070 mmol) in dioxane (1 mL) was added 1N NaOH (0.700 mL) and the reaction was stirred at 75° C. After 1 h, the mixture was cooled to room temperature and neutralized with 0.7 ml 1M HCl then concentrated. The crude material was purified via preparative LC/MS with the following conditions: Column. Waters XBridge C18, 19×200 mm, 5-μm particles; Guard Column. Waters XBridge C18, 19×10 mm, 5-μm particles; Mobile Phase A: water with 20-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 20-mM ammonium acetate; Gradient: 30-100% B over 12 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation 1H NMR (500 MHz, DMSO-d6) δ ppm 7.29-7.38 (m, 2H), 7.21-7.26 (m, 2H), 7.09-7.21 (m, 5H), 4.77 (s, 1H), 3.26 (s, 1H), 2.95 (d, J=14.95 Hz, 1H), 2.88 (br. s., 3H), 2.62-2.76 (m, 3H), 2.58 (d, J=7.02 Hz, 2H), 2.48 (s, 3H), 2.40 (s, 3H), 0.87 (s, 9H). LCMS (M+H) calcd for C30H37N2O3: 473.28. found: 473.1.

Provenance & Evidence