Hydrochloric Acid → (S)-4-methyl-1((2-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-amine

Participants

Reaction Steps

To a stirred solution of (S)-tert-butyl (4-methyl-1-((2-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)carbamate (0.05 g, 0.121 mmol) in MeOH (2 mL) was added 4N HCl in 1,4-dioxane (0.5 mL, 16.46 mmol). The reaction mixture was stirred for 4 h at RT. The reaction mixture was then concentrated and the residue was dissolved in ethyl acetate (10 mL). The organic layer was washed with saturated NaHCO3 (2×10 mL) and water (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford a residue which was purified by prep. HPLC (0.1% ammonium acetate in acetonitrile) to afford (S)-4-methyl-1((2-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-amine (0.15 g, 0.048 mmol, 32% yield) as a gummy-solid. 1H NMR (400 MHz, CD3OD) δ 8.21 (s, 1H); 7.80 (d, J=8.80 Hz, 1H), 7.55 (s, 1H); 6.74 (d, J=10.80 Hz, 1H), 6.60 (d, J=2.40 Hz, 1H), 5.12 (s, 2H), 4.01-3.96 (m, 1H), 3.84-3.79 (m, 1H), 3.24-3.22 (m, 1H), 2.53 (s, 3H), 1.82-1.79 (m, 1H), 1.42-1.39 (m, 2H), 0.99-0.95 (m, 6H); LCMS (ESI) m/e 312.5 [(M)+, calcd for C19H24N2O2 312.2]; LC/MS retention time (Method E): tR=1.63 min; HPLC retention time (method A): tR=7.96 min; HPLC retention time (method B): tR=9.01 min.

Provenance & Evidence