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

Participants

Reaction Steps

In a similar manner to that described in example 196, from ethyl 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.075 mmol) and N-(2-aminoethyl)-N-methylmethanesulfonamide (excess) was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (21 mg, 55% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.41 (br s, 1 H), 8.55 (s, 1 H), 7.27 (s, 1 H), 7.17-7.13 (m, 2 H), 7.05-7.00 (m, 2 H), 4.13 (s, 2 H), 4.08 (m, 2 H), 3.65 (m, 2 H), 3.39 (m, 2 H), 2.94 (s, 3 H), 2.82(s, 3 H), 1.50 (m, 2 H), 1.33 (m, 2 H), 0.89 (m, 3 H); MS m/z 505 (M+1).

Provenance & Evidence