2-Morpholinoethylamine → 7(4-Fluorobenzyl)-4-hydroxy-N-(2-morpholin-4-ylethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

This compound was prepared from ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-(4-morpholino)ethylamine employing methods similar to those described in Example 5. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). This procedure gave the product as an off-white rigid foam: 1H NMR (CDCl3) δ 10.46 (1H, br t, J˜6 Hz), 8.59 (1H, d, J=1.3 Hz), 8.12 (1H, s), 7.24 (2H, dd, J=8.6, 5.4 Hz), 7.00 (2H, t, J=8.6 Hz), 4.32 (2H, br t, J=7 Hz), 4.16 (2H, s), 3.98 (4H, br), 3.91 (2H, q, J=6 Hz), 3.77 (2H, br), 3.50 (4H, m), 3.39 (2H, t, J=6 Hz), 2.92 (2H, br), 2.41 (2H, t, J=8 Hz), 2.05 (2H, m); ES+ MS: 538 (M+H+, 100).

Provenance & Evidence