Trifluoroacetic acid → HCID 59375596, compound

Participants

Reaction Steps

To a solution of tert-butyl (3S)-3-{[4-(cyclopropylethynyl)-1-oxo-1,2-dihydropyrido[4,3-c]-1,6-naphthyridin-6-yl]amino}piperidine-1-carboxylate (100 mg, 0.218 mmol) in dichloromethane (2 mL), trifluoroacetic acid (2000 26.0 mmol) was added. After stirring at room temperature for 10 min, the mixture was quenched with aqueous sodium hydrogen carbonate (saturated). The aqueous layer 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 4-(cyclopropylethynyl)-6-[(3S)-piperidin-3-ylamino]pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one as a yellow solid. 1H NMR (500 MHz, C2D6SO) δ 10.97 (s, 1H), 8.74 (d, 1H), 8.29 (d, 1H), 8.06 (d, 1H), 7.61 (s, 1H), 4.42 (m, 1H), 3.03 (m, 2H), 2.74 (m, 1H), 2.16 (t, 2H), 1.66 (m, 2H), 0.84 (m, 6H). LRMS (APCI) calc'd for (C21H22N5O) [M+H]+, 360.2; found 360.1.

Provenance & Evidence