1-(3-Aminopropyl)-2-pyrrolidinone → HCID 69480956, 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-(3-aminopropyl)-2-pyrrolidinone (0.0085 mL, 0.061 mmol) for 30 min. 150° C. The reaction was further microwaved for 30 min.@150° C. after the addition of an additional equivalent (0.0085 mL) of the amine, cooled to ambient temperature, and treated with 1N NaHSO4. The resulting suspension was filtered, washed with EtOH 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 1.74 (ddd, J=12.42, 6.11, 5.90 Hz, 2 H), 1.84-1.95 (m, 2 H), 1.99-2.12 (m, 4 H), 2.41 (td, J=8.14, 2.25 Hz, 4 H), 3.21-3.32 (m, 2 H), 3.35-3.50 (m, 10 H), 3.61-3.73 (m, 2 H), 4.07 (s, 2 H), 4.48 (t, J=6.74 Hz, 2 H), 6.91-7.01 (m, 2 H), 7.17-7.23 (m, 2 H), 7.47-7.62 (m, 4 H), 7.71 (dd, J=5.26, 3.44 Hz, 1 H), 7.77 (t, J=5.90 Hz, 1 H), 8.18 (s, 1 H), 8.49 (s, 1 H), 10.31 (t, J=5.76 Hz, 1 H); ES+ MS: 754 (M+H+).

Provenance & Evidence