Trifluoroacetic acid → HCID 69296327, compound

Participants

Reaction Steps

The above prepared 3-(3-amino-4-fluoro-phenyl)-1-isopropyl-7-[(4-methoxy-benzyl)-methyl-amino]-1H-[1,6]naphthyridin-2-one (5.3 g) was combined in DCM (150 mL) with TFA (50 mL) and the resultant mixture was heated at reflux overnight. The volatiles were removed under reduced pressure, and the residue was dissolved in 10% HCl aqueous solution. The aqueous layer was washed with EtOAc (3×100 mL) and the aqueous layer was basified to pH 11, and extracted with EtOAc. The combined extracts were dried (Na2SO4) and concentrated to give 3-(3-amino-4-fluoro-phenyl)-1-isopropyl-7-methylamino-1H-[1,6]naphthyridin-2-one (1.26 g, 32% yield for two steps). 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1 H), 7.70 (s, 1 H), 7.06 (dd, J=8.4, 2.0 Hz, 1 H), 6.94 (dd, J=11.6, 8.4 Hz, 1 H), 6.88 (m, 1 H), 6.72 (m, 1 H), 6.39 (s, 1 H), 5.07 (m, 1 H), 5.06 (s, 2 H), 2.83 (d, J=4.8 Hz, 1 H), 1.51 (d, J=6.8 Hz, 6 H); MS (ESI) m/z: 327.1 [M+H]+.

Provenance & Evidence