N-(2-aminoethyl)acetamide → N-[2-(acetylamino)ethyl]-1-{4-[(dimethylamino)carbonyl]phenyl}-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 from methyl 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (8 mg, 0.0168 mmol), N-(2-aminoethyl)acetamide (10 mg, 0.098 mmol) and methanol (2 mL), was prepared N-[2-(acetylamino)ethyl]-1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (4.9 mg, 54% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.14 (m, 1 H), 8.52 (s, 1 H), 7.65 (d, J=8.4 Hz, 2 H), 7.27 (d, J=8.4 Hz, 2 H), 7.02-6.98 (m, 2 H), 6.95-6.90 (m, 2 H), 6.79 (s, 1 H), 6.03 (br s, 1 H), 3.94 (s, 2 H), 3.57-3.54 (m, 2 H), 3.47-3.42 (m, 2 H), 3.16 (s, 3 H), 3.04 (s, 3 H), 1.95 (s, 3 H); MS m/z 546 (M+1).

Provenance & Evidence