Hydrochloric Acid → HCID 73213801, compound

Participants

Reaction Steps

An ambient temperature solution of (R)-tert-butyl (1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (102 mg, 0.232 mmol) in dichloromethane (1 mL) was treated with HCl (1.160 mL, 4.64 mmol) and stirred for 1 h. The resulting mixture was concentrated to an oil and purified by reverse phase high performance liquid chromatography (Phenomenex Luna C18 30×100 mm 10 micron; water/methanol/0.1% TFA gradient elution). Fractions containing product were neutralized with saturated aqueous sodium bicarbonate and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and brine and the layers were separated. The aqueous was extracted twice more with ethyl acetate and the pooled organics were washed once with brine, dried over magnesium sulfate, filtered, and concentrated to afford (R)-8-((2-amino-4-methylpentyl)oxy)-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (11.5 mg, 0.033 mmol, 14% yield) as a milky oil. LC/MS, (ESI) m/z 340.2 [(M+H)+, calcd for C20H26N3O2 340.2]; HPLC retention time (method C): tR=13.02 min; HPLC retention time (method D): tR=13.05 min; 1H NMR (500 MHz, METHANOL-d4) δ 8.68-8.63 (m, 2H), 8.58 (d, J=9.0 Hz, 1H), 7.22 (dd, J=9.0, 2.3 Hz, 1H), 7.20 (d, J=2.3 Hz, 1H), 4.52 (dd, J=10.5, 3.3 Hz, 1H), 4.34 (dd, J=10.7, 6.6 Hz, 1H), 3.82 (s, 3H), 3.80-3.75 (m, 1H), 3.25 (s, 3H), 1.91-1.81 (m, 1H), 1.80-1.73 (m, 1H), 1.72-1.64 (m, 1H), 1.07 (d, J=5.8 Hz, 3H), 1.06 (d, J=5.8 Hz, 3H).

Provenance & Evidence