N-(2-aminoethyl)-N-methylmethanesulfonamide → 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

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Reaction Steps

In a manner similar to that described in example 316, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (10 mg, 0.025 mmol) and N-(2-aminoethyl)-N-methylmethanesulfonamide (50 mg, 0.329 mmol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-1-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (8 mg, 62% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.36 (br s, 1 H), 8.53 (s, 1 H), 7.69 (s, 1 H), 7.16-7.13 (m, 2 H), 7.02-6.98 (m, 2 H), 4.33 (m, 2 H), 4.10 (s, 2 H), 3.68-3.61 (m, 4 H), 3.39 (m, 2 H), 3.18 (s, 3 H), 2.95 (s, 3 H), 2.82 (s, 3 H); MS m/z 507 M+1).

Provenance & Evidence