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

Participants

Reaction Conditions

Reaction Steps

(S)-tert-butyl (4-methyl-1-((5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (10 mg, 0.024 mmol) in dichloromethane (1 mL) was cooled to 0° C. To the solution was added hydrogen chloride (0.886 mg, 0.012 mL, 0.024 mmol, 2M in diethyl ether) dropwise. The temperature of the reaction mixture was maintained at 0° C. for 30 min and then 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 (S)-8-((2-amino-4-methylpentyl)oxy)benzo[c][2,7]naphthyridin-5(6H)-one (4 mg, 0.012 mmol, 49% yield) as a pale yellow solid. LC/MS (ESI) m/e 312.2 [(M+H)+, calcd for C18H22N3O2 312.2]; LC/MS retention time (method A): tR=1.1 min; HPLC retention time (method A): tR=6.85 min; HPLC retention time (method B): tR=7.51 min 1H NMR (400 MHz, D2O) δ ppm 9.30 (br. s., 1H), 8.77 (br. s., 1H), 8.36 (br. s., 1H), 8.07 (br. s., 1H), 6.95 (br. s., 1H), 6.72 (br. s., 1H), 4.41 (d, J=9.03 Hz, 1H), 4.26 (br. s., 1H), 3.89 (br. s., 1H), 3.38 (s, 1H), 1.72-1.88 (m, 2H), 1.05 (d, J=2.51 Hz, 6H).

Provenance & Evidence