N-benzyl-1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-amine → 6-(benzylamino)pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one

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Reaction Steps

N-benzyl-1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (90 mg, 0.251 mmol) was dissolved in hydrobromic acid (2.5 mL, 33% in acetic acid). The reaction mixture was left to stir overnight at room temperature. The reaction mixture was quenched with aqueous sodium hydrogen carbonate. The aqueous mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford 6-(benzylamino)pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one as a red solid. 1H NMR (500 MHz, C2D6SO) δ 11.39 (d, 1H), 11.00 (s, 1H), 8.94 (t, 1H), 8.72 (d, 1H), 8.24 (d, 1H), 7.40 (t, 3H), 7.30 (t, 2H), 7.22 (t, 1H), 6.39 (d, 1H), 4.82 (d, 2H). LRMS (APCI) calc'd for (C18H15N4O) [M+H]+, 303.1; found 303.1.

Provenance & Evidence