1-Propanol, 3-amino-2,2-dimethyl- → 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

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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 3-amino-2,2-dimethyl-1-propanol (0.05 mL) was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (18 mg, 53% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.51 (br s, 1 H), 8.56 (s, 1 H), 7.27 (s, 1 H), 7.17-7.13 (m, 2 H), 7.05-7.01 (m, 2 H), 4.14 (s, 2 H), 4.08 (m, 2 H), 3.39 (m, 1 H), 3.30 (m, 2 H), 3.22 (m, 2 H), 1.51 (m, 2 H), 1.33 (m, 2 H), 0.94 (s, 6 H), 0.90 (m, 3 H); MS m/z 456 M+1).

Provenance & Evidence