L-Alaninol → 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-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-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (60 mg, 0.162 mmol) and (2S)-2-amino-1-propanol (0.05 mL) was prepared 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (33 mg, 51% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.27 (d, J=7.6 Hz, 1 H), 8.50 (s, 1 H), 7.33 (s, 1 H), 7.16-7.12 (m, 2 H), 7.04-6.98 (m, 2 H), 4.27 (m, 6 H), 3.78 (dd, J=11.2, 3.6 Hz, 1 H), 3.65 (dd, J=11.2, 6 Hz, 1 H), 1.29 (d, J=6.8 Hz, 3 H), 1.19 (m, 3 H); MS m/z 400 (M+1).

Provenance & Evidence