Hydrochloric Acid → HCID 72737640, compound

Participants

Reaction Steps

To a stirred solution of (S)-tert-butyl (1-((9-fluoro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (25 mg, 0.056 mmol) in diethyl ether (4 mL) was added a 2M solution of hydrochloric acid in diethyl ether (42.5 μl, 0.085 mmol) at 0° C. dropwise over 10 min. The ice bath was removed and the reaction mixture was stirred at room temperature for 2 h. The solvent was removed and the crude material was taken up in water (5 mL). The aqueous layer was washed with ethyl acetate (3 mL) and treated with 10% NaHCO3 (20 mL). The resultant solution was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (2×10 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure to afford crude material which was purified via preparative TLC (40% Ethyl acetate in Hexane) to afford (S)-8-((2-amino-4-methylpentyl)oxy)-9-fluoro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (15 mg, 0.041 mmol, 73% yield) as a white solid. LC/MS (ESI) m/e 344.2 [(M+H)+, calcd for C19H23FN3O2 344.2]; LC/MS retention time (method A): tR=1.35 min; HPLC retention time (method A): tR=8.31 min; HPLC retention time (method B): tR=8.85 min; 1H NMR (400 MHz, CD3OD) δ ppm 9.66-9.71 (m, 1H), 8.83-8.87 (m, 1H), 7.90-7.95 (m, 1H), 7.79-7.83 (m, 1H), 6.91-6.95 (m, 1H), 4.10-4.14 (m, 1H), 3.89-3.95 (m, 1H), 3.76-3.80 (m, 3H), 3.35-3.44 (m, 1H), 1.78-1.86 (m, 1H), 1.39 (t, J=7.00 Hz, 2H), 0.96-1.03 (m, 6H).

Provenance & Evidence