Trifluoroacetic acid → HCID 69035893, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of TFA in CH2Cl2 (10%, 50 mL) was added 3-(3-amino-4-fluoro-phenyl)-1-ethyl-7-(4-methoxy-benzylamino)-1H-[1,6]naphthyridin-2-one (2.0 g, 4.78 mmol). The resulting mixture was stirred at 50° C. overnight. The reaction mixture was poured saturated aq NaHCO3 solution (100 mL), and was extracted with CH2Cl2 (3×75 mL). The combined organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography to give 7-amino-3-(3-amino-4-fluorophenyl)-1-ethyl-1,6-naphthyridin-2(1H)-one (0.45 g, 32% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.35 (s, 1 H), 7.76 (s, 1 H), 7.09 (dd, J=9.0, 2.1 Hz, 1 H), 6.97 (dd, J=11.4, 8.4 Hz, 1 H), 6.75 (m, 1 H), 6.44 (s, 2 H), 6.31 (s, 1 H), 5.09 (s, 2 H), 4.08 (q, J=7.2 Hz, 2 H), 1.20 (t, J=7.2 Hz, 3 H), MS (ESI) m/z (M+H+): 299.3.

Provenance & Evidence