Trifluoroacetic acid → HCID 69299467, compound

Participants

Reaction Steps

7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1, 6-naphthyridin-2(1H)-one (1.86 g, 4.3 mmol, 1.0 eq) and CF3CO2H (9.5 ml, 13.8 g, 121 mmol, 28 eq) were combined and stirred at RT overnight. The completed reaction was treated slowly with 2M Na2CO3 until the mixture was just faintly basic. The resulting suspension was stirred at RT for 1 h. The solids were collected by filtration, washed thoroughly with H2O, dried partially in the air and then under high vacuum at 65° C. The crude product was purified by flash column chromatography (100% EtOAc to 25% THF/EtOAc) to afford 3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (0.86 g, 64% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.35 (s, 1H), 7.58 (s, 1H), 6.99 (q, J=4.8 Hz, 1H), 6.56 (d, J=12.0 Hz, 1H), 6.56 (d, J=9.2 Hz, 1H), 6.15 (s, 1H), 4.87 (brs, 2H), 3.48 (s, 3H), 2.84 (d, J=5.2 Hz, 3H), 1.94 (s, 3H); MS (ESI) m/z: 313.2 (M+H+).

Provenance & Evidence