(2R)-1-aminopropan-2-ol → 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2R)-2-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 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.075 mmol) and (2R)-1-amino-2-propanol (0.05 mL) was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(2R)-2-hydroxypropyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (20 mg, 63% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.48 (br s, 1 H), 8.56 (s, 1 H), 7.27 (s, 1 H), 7.19-7.15 (m, 2 H), 7.06-7.02 (m, 2 H), 4.14 (s, 2 H), 4.10-4.06 (m, 3 H), 3.61 (m, 1 H), 3.66 (m, 1 H), 1.52 (m, 2 H), 1.34 (m, 2 H), 1.27 (d, J=6.4 Hz, 3 H), 0.91 (m, 3 H); MS m/z 428 (M+1).

Provenance & Evidence