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0 °C

To a solution of tert-butyl (1-((7-fluoro-4,6-dimethyl-5-oxo-5,6 dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-2,4-dimethylpentan-2-yl)carbamate (200 mg, 0.424 mmol) in MeOH (6 mL) at 0° C. was added 4M HCl in 1,4-dioxane (3 mL, 99.0 mmol). The reaction mixture was stirred at 0° C. for 2 h. After 2 h, the reaction mixture was concentrated under reduced pressure to afford crude product which was purified by preparative HPLC to afford 8-((2-amino-2,4-dimethylpentyl)oxy)-7-fluoro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (10 mg, 0.024 mmol, 6% yield) as an off-white solid. LC/MS (ESI) m/e 372.0 [(M+H)+, calcd for C21H27FN3O2 372.2]; LC/MS retention time (method G): tR=1.99 min. HPLC retention time (method A): tR=8.37 min; HPLC retention time (method B): tR=9.72 min. 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.58 (d, J=6 Hz, 1H), 8.22 (dd, J=9.2 Hz, J=2 Hz, 1H), 8.14 (d, J=6 Hz, 1H), 7.23 (m, 1H), 4.31 (d, J=10 Hz, 1H), 4.23 (d, J=10.4 Hz, 1H), 3.88 (d, J=9.2 Hz, 3H), 3.06 (s, 3H), 1.90 (m, 2H), 1.73 (m, 1H), 1.52 (s, 3H), 1.05 (m, 6H).

1. waitAfter 2 h
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. customto afford crude product which
4. customwas purified by preparative HPLC