N-(2-aminoethyl)acetamide → N-[2-(acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-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-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (60 mg, 0.15 mmol) and N-(2-aminoethyl)acetamide (100 mg, 0.99 mmol) was prepared N-[2-(acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (21 mg, 31% yield) as a tan solid after purification by reverse phase HPLC. 1H NMR (methanol-d4/CDCl3) δ 10.18 (br s, 1 H), 8.40 (s, 1 H), 7.56 (s, 1 H), 7.09-7.05 (m, 2 H), 6.94-6.88 (m, 2 H), 4.21 (m, 2 H), 4.04 (s, 2 H), 7.70 (m, 2 H), 3.46 (m, 2 H), 3.33 (m, 2 H), 1.86 (s, 3 H), 1.74 (m, 2 H); MS m/z 457 M+1).

Provenance & Evidence