Hydrochloric Acid → (S)-8-((2-amino-4-methylpentyl)oxy)-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl (4-methyl-1-((6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (190 mg, 0.447 mmol) in dichloromethane (4 mL) at 0° C. was added hydrogen chloride (81 mg, 0.558 mL, 2.233 mmol) in 1,4-dioxane (4 M) dropwise and the reaction mixture was stirred at 0° C. for 30 min then warmed to room temperature and allowed to stir for 2 h. The solvents were removed under reduced pressure to afford crude product which was purified by preparative HPLC (0.1% TFA in water) to afford (S)-8-((2-amino-4-methylpentyl)oxy)-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (51 mg, 0.157 mmol, 35% yield) as a yellow solid. LC/MS (ESI) m/e 326.2 [(M+H)+, calcd for C19H24N3O2 326.2]; LC/MS retention time (method A): tR=1.21 min; HPLC retention time (method A): tR=7.39 min; HPLC retention time (method B): tR=7.40 min. 1H NMR (400 MHz, CD3OD) δ ppm 9.48 (s, 1H), 8.77 (d, J=5.77 Hz, 1H), 8.43 (d, J=8.78 Hz, 1H), 8.26 (d, J=5.77 Hz, 1H), 7.09-7.16 (m, 2H), 4.20 (dd, J=9.41, 3.89 Hz, 1H), 4.02 (dd, J=9.29, 7.03 Hz, 1H), 3.81 (s, 3H), 3.35-3.39 (m, 1H), 1.81-1.91 (m, 1H), 1.41-1.56 (m, 2H), 0.98-1.05 (m, 6H).

Provenance & Evidence