2-Methoxyethylamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-[2-(methyloxy)ethyl]-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 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 [2-(methyloxy)ethyl]amine (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (21 mg, 33% yield) as a yellow solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.22 (br s, 1 H), 8.56 (s, 1 H), 7.46 (s, 1 H), 7.16-7.16 (m, 2 H), 7.03-6.99 (m, 2 H), 4.31 (m, 2 H), 4.12 (s, 2 H), 3.64 (m, 2 H), 3.57 (m, 2 H), 3.49 (m, 2 H), 3.39 (s, 3 H), 1.82 (m, 2 H); HRMS m/z calcd for C22H25N3O5F: 430.1778. Found: 430.1778.

Provenance & Evidence