1-(3-Aminopropyl)-2-pyrrolidinone → 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

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), 1-(3-aminopropyl)-2-pyrrolidinone (0.05 mL), and methanol (2 mL), was prepared 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (20 mg, 80% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.04 (t, J=6 Hz, 1 H), 8.51 (d, J=1.6 Hz, 1 H), 7.65 (d, J=8.4 Hz, 2 H), 7.28 (d, J==8.4 Hz, 2 H), 7.03-6.99 (m, 2 H), 6.96-6.91 (m, 2 H), 6.79 (d, J=1.6 Hz, 1 H), 3.94 (s, 2 H), 3.45-3.33 (m, 6 H), 3.16 (s, 3 H), 3.06 (s, 3 H), 2.36 (t, J=8 Hz, 2 H), 2.05-1.97 (m, 2 H), 1.87-1.80 (m, 2 H); MS m/z 586 (M+1).

Provenance & Evidence