Trifluoroacetic acid → HCID 69297968, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (2 mL, 26.9 mmol) was added to a solution of 7-(4-methoxybenzylamino)-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (0.8 g, 1.9 mmol) in DCM (10 mL) and the reaction mixture was refluxed at 50° C. for 2 hour. After cooling to RT, the reaction mixture was washed with water and the combined aqueous layers were neutralized with saturated aq NaHCO3 to pH 7-8. Then the aqueous layer was extracted with EtOAc (3×50 mL), the extracts were dried (Na2SO4) and concentrated to give 7-amino-3-(5-amino-4-fluoro-2-methylphenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (0.3 g, 53% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.29 (s, 1H), 7.57 (s, 1 H), 6.83 (d, J=12.4 Hz, 1 H), 6.56 (d, J=9.6 Hz, 1 H), 6.48 (s, 2 H), 6.24 (s, 1 H), 4.87 (s, 2 H), 3.45 (s, 3 H), 1.94 (s, 3 H); MS (ESI) m/z: 299.0 [M+H]+.

Provenance & Evidence