Hydrochloric Acid → HCID 73213729, compound

Participants

Reaction Steps

To a solution of (S)-tert-butyl (1-((7,9-dichloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (0.120 g, 0.243 mmol) in anhydrous methanol (5 mL) was added a 4M solution of HCl in 1,4-1,4-dioxane (2 mL, 8 mmol) dropwise at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was then concentrated under reduced pressure to afford crude compound which was purified by preparative HPLC (10 mM ammonium acetate in water; acetonitrile) to afford (S)-8-((2-amino-4-methylpentyl)oxy)-7,9-dichloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (28 mg, 0.063 mmol, 26% yield) as a yellow solid. LC/MS (ESI) m/e 394.2 [(M+H)+, calcd for C19H22Cl2N3O2 394.1]; LC/MS retention time (method A): tR=1.48 min; HPLC retention time (method A): tR=5.21 min; HPLC retention time (method B): tR=5.73 min. 1H NMR (400 MHz, CD3OD) δ ppm 9.50 (d, J=0.75 Hz, 1H), 8.87 (d, J=5.52 Hz, 1H), 8.58 (s, 1H), 8.32 (d, J=5.27 Hz, 1H), 4.17 (dd, J=9.03, 4.02 Hz, 1H), 4.05 (dd, J=9.03, 7.28 Hz, 1H), 3.93 (s, 3H), 3.37-3.43 (m, 1H), 1.82-1.93 (m, 1H), 1.38-1.57 (m, 2H), 0.99-1.05 (m, 6H).

Provenance & Evidence