N-(2-Aminoethyl)ethyleneurea → HCID 69480250, compound

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 1-(2-aminoethyl)-2-imidazolidinone (0.0078 g, 0.03 mmol, 50% W/W in IPA) for 30 min.@150° C. The reaction was further microwaved for 30 min.@150° C. after the addition of an additional 0.6 equivalents (0.015 mL) of the amine, cooled to ambient temperature, and treated with 1N NaHSO4. The resulting suspension was filtered and the filtrate was concentrated in vacuo. The filtrate residue was purified by reversed phase HPLC. Pure fractions were combined and concentrated to afford the title compound as a pale yellow glass: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.82 (s, 1 H), 3.38-3.51 (m, 4 H), 3.52-3.65 (m, 4 H), 4.00 (t, J=6.67 Hz, 2 H), 4.04-4.10 (m, 2 H), 4.26 (s, 1 H), 4.46 (t, J=6.74 Hz, 2 H), 6.91-7.04 (m, 2 H), 7.10-7.21 (m, 2 H), 7.70-7.78 (m, 3 H), 7.79-7.85 (m, 2 H), 8.51 (d, J=1.26 Hz, 1 H), 10.24 (t, J=6.04 Hz, 1 H); ES+ MS: 599 (M+H+).

Provenance & Evidence