Trifluoroacetic acid → HCID 69296251, compound

Participants

Reaction Steps

Trifluoroacetic acid (10 mL, 134 mmol) was added to a solution of 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chlorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (4 g, 9.2 mmol) in CH2Cl2 (50 mL). The mixture was heated to reflux for 3 hrs. The reaction mixture was concentrated under reduced pressure, dissolved in aq HCl solution and washed with EtOAc (3×50 mL). The aqueous layer was neutralized with saturated Na2CO3 solution to pH 8, and was extracted with EtOAc (3×50 mL). The combined extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography to give 3-(5-amino-2-chlorophenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (1.7 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1 H), 7.63 (s, 1 H), 7.06-7.00 (m, 2 H), 6.54-6.50 (m, 2 H), 6.14 (s, 1 H), 5.21 (s, 2 H), 3.48 (s, 3 H), 2.84 (d, J=4.8 Hz, 3 H); MS (ESI) m/z: 314.9 [M+H]+.

Provenance & Evidence