2-Morpholinoethylamine → 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

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Reaction Steps

In a similar manner to that described in example 196, from methyl 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.0421 mmol), [2-(4-morpholinyl)ethyl]amine (0.05 mL), and methanol (2 mL), was prepared 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (20 mg, 83% yield) as a tan solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.02 (br s, 1 H), 8.50 (s, 1 H), 7.64 (d, (J=8.4 Hz, 2 H), 7.26 (d, J=8.4 Hz, 2 H), 7.01-6.98 (m, 2 H), 6.94 (m, 2 H), 6.77 (s, 1 H), 3.93 (s, 2 H), 3.71-3.68 (m, 4 H), 3.58 (q, J=12.4, 6.4 Hz, 2 H), 3.15 (s, 3 H), 3.05 (s, 3 H), 2.63 (t, J=6.4 Hz, 2 H), 2.56-2.54 (m, 4 H); MS m/z 574 (M+1).

Provenance & Evidence