N-(2-aminoethyl)-N-methylmethanesulfonamide → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-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 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.056 mmol) described in example 92 and N-(2-aminoethyl)-N-methylmethanesulfonamide (55 mg, 0.364 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2[methyl(methylsulfonyl)amino]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (24 mg, 96% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.39 (br s, 1 H), 8.55 (s, 1 H), 7.38 (s, 1 H), 7.16-7.12 (m, 2 H), 7.03-6.99 (m, 2 H), 4.12 (s, 2 H), 3.68-3.63 (m, 2 H), 3.56 (s, 3 H), 3.42-3.38 (m, 2 H), 2.94 (s, 3 H), 2.82 (s, 3 H). HRMS m/z calcd for C21H24N4O5FS: 463.1451; Found: 463.1443.

Provenance & Evidence