Nitric Acid → HCID 59375493, compound

Participants

Reaction Conditions

Reaction Steps

Nitric acid (0.271 mL, 4.24 mmol) was added to 9-bromo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (397 mg, 1.061 mmol) in TFA (10.600 mL) at room temperature. Reaction was then heated to 40° C. and stirred for 1.5 h. The reaction was then diluted with dichloromethane (150 mL) and quenched by pouring cautiously into saturated NaHCO3. The layers were separated and the aqueous phase was further extracted with a 75 mL portion of dichloromethane. The combined organic layers were then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, loading with THF/hexanes and eluting with EtOAc/Hexanes to give the title compound as an orange solid. 1H NMR (500 MHz, C2D6SO) δ 12.11 (s, 1H), 9.98 (d, 1H, J=2.0 Hz), 8.55 (d, 11-1, J=9.0 Hz), 8.44 (s, 1H), 7.95 (d, 1H, J=9.0 Hz), 7.85 (dd, 1H, J=8.5, 2.0 Hz), 4.69 (m, 1H), 1.17 (d, 3H, J=7.0 Hz), 0.94 (s, 9H). LRMS (ESI) calc'd for (C18H20BrN4O3) [M+H]+ 419.1; found 419.0.

Provenance & Evidence