Cyclopropylamine → N-Cyclopropyl-7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate (47 mg, 104 μmol) and cyclopropylamine (0.1 mL, 1.44 mmol) in EtOH (3 mL) was heated at 120° C. in a microwave for 20 min. The mixture was concentrated in vacuo, triturated with EtOH and the product was collected by filtration as a white solid: 1H NMR (CDCl3) δ 10.06 (1H, d, J=3 Hz), 8.57 (1H, d, J=1.2 Hz), 8.08 (1H, s), 7.25 (2H, dd, J=8.5, 5.5 Hz), 7.00 (2H, t, J=8.5 Hz), 4.32 (2H, q, J=7 Hz), 4.14 (2H, s), 3.49 (2H, t, J=7.4 Hz), 3.41 (2H, t, J=7 Hz), 2.95 (1H, m), 2.32 (2H, t, J=8 Hz), 1.97 (2H, m), 0.90 (2H, m), 0.69 (2H, m); HRMS calcd for C25H25FN4O4+H+: 465.1938. Found: 465.1932.

Provenance & Evidence