Diglycolamine → 1-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(2-hydroxyethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

A solution of 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 (0.025 g, 0.049 mmol) in EtOH (1 mL) under nitrogen was treated with 2-[(2-aminoethyl)oxy]ethanol (0.0042 mL, 0.058 mmol) for 10 min.@150° C. in a microwave vessel. An additional 0.001 mL of the amine was added to the reaction and it was further microwaved for 20 min.@150° C. The reaction was then cooled to ambient temperature and the resulting suspension was filtered, washed with 1:1 water:EtOH and then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 3.35-3.44 (m, 6 H), 3.44-3.51 (m, 2 H), 3.90 (t, J=5.05 Hz, 2 H), 4.11 (s, 2 H), 4.50-4.62 (m, 3 H), 7.08-7.17 (m, 2 H), 7.30-7.38 (m, 2 H), 7.82 (s, 4 H), 8.14 (s, 1 H), 8.52 (s, 1 H), 10.02 (m, 1 H), 17.11 (s, 1 H); ES+ MS: 575 (M+H+).

Provenance & Evidence