Hydrochloric Acid → HCID 178525986, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-2-hydroxy-4-oxobut-2-enoate 7 (2.59 g, 5.7 mmol) in 1,4-dioxane (125 ml) was added 1N HCl (63 ml). The reaction mixture was allowed to stir at 95° C. for 2 h. The crude product was extracted with ethyl acetate (250 ml). The solvent was evaporated under reduced pressure. The solid was crystallized in chloroform and filtered under reduced pressure. Yield 1.61 g (64%). Yellow solid, mp 187-189° C., UV (MeOH) 394 nm (ε 14,917), 320 (ε 5671). 1H NMR (CDCl3-MeOH-d4, 500 MHz): δ 8.17 (d, 1H, J=3.4 Hz), 7.88 (s, 1H), 7.54 (s, 1H), 7.48-7.45 (m, 1H), 7.36-7.30 (m, 1H), 7.17-7.07 (m, 3H), 6.87-6.81 (m, 2H), 5.19 (s, 2H), 3.76 (s, 2H). 13C NMR (DMSO-d6, 125 MHz): δ 184.5, 173.3, 163.2, 161.7, 161.2, 159.8, 158.6, 144.6, 131.9, 130.0, 129.8, 124.5, 123.1, 123.0, 121.5, 116.8, 115.4, 111.6, 103.9, 100.8, 47.3, 29.2. HRMS [M+H]+ calculated mass 444.1059 for C23H17F3NO5. found 444.1042.

Provenance & Evidence