1-(3-Aminopropyl)-2-pyrrolidinone → 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-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 ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (15 mg, 0.0344 mmol) and 1-(3-aminopropyl)-2-pyrrolidinone (0.05 mL) was prepared 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (10 mg, 56% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.03 (t, J=5.6 Hz, 1 H), 8.50 (s, 1 H), 7.29-7.17 (m, 2 H), 7.20-7.16 (m, 2 H), 7.01-6.91 (m, 4 H), 6.69 (s, 1 H), 3.93 (s, 2 H), 3.44-3.32 (m, 6 H), 2.35 (t, J=8 Hz, 2 H), 2.04-1.96 (m, 2 H), 1.89-1.78 (m, 2 H); MS m/z 533 (M+1).

Provenance & Evidence