1,8-Diazabicyclo(5.4.0)undec-7-ene → ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Participants

Reaction Steps

A solution of ethyl 3-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl][3-(ethyloxy)-3-oxopropanoyl]amino}-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (2.05 g, 3.65 mmol) in EtOH (75 mL) under nitrogen was treated with DBU (0.709 mL, 4.74 mmol). After stirring at ambient temperature for 15 min., the reaction mixture was treated with 1N NaHSO4 (5.0 mL). The resulting slurry was diluted with water, filtered, the filtered solid was washed with water, EtOH, and Et2O and thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.4 (t, J=7.0 Hz, 3 H), 4.0 (t, J=7.0 Hz, 4 H), 4.4 (t, J=6.5 Hz, 2 H), 4.5 (q, J=7.3 Hz, 2 H), 7.0 (t, J=8.5 Hz, 2 H), 7.1 (m, 2 H), 7.7 (dd, J=5.5, 3.1 Hz, 2 H), 7.8 (s, 1 H) 7.8 (m, 2 H), 8.4 (s, 1 H), 13.9 (none, 1 H); ES+ MS: 516 (M+H+).

Provenance & Evidence