N-(2-aminoethyl)acetamide → N-[2-(acetylamino)ethyl]-1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-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)acetamide (27 mg, 0.264 mmol) was prepared N-[2-(acetylamino)ethyl]-1-butyl-7-[(4fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (20 mg, 59% 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), 8.17-7.13 (m, 2 H), 7.05-7.01 (m, 2 H), 6.18 (br s, 1 H), 4.13 (s, 2 H), 4.06 (m, 2 H), 3.59 (m, 2 H), 3.47 (m, 2 H), 1.97 (s, 3 H), 1.52 (m, 2 H), 1.33 (m, 2 H), 0.90 (m, 3 H); MS m/z 455 (M+1).

Provenance & Evidence