1-Amino-2-propanol → 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-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-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.081 mmol) and 1-amino-2-propanol (0.05 mL) was prepared 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (12 mg, 38% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.49 (s, 1 H), 8.56 (s, 1 H), 7.37 (s, 1 H), 7.18 (m, 2 H), 7.05-7.07 (m, 2 H), 4.23-4.06 (m, 5 H), 3.62 (m, 1 H), 3.38 (m, 1 H), 1.29-1.22 (m, 6 H); HRMS m/z calcd for C21H23FN3O4: 400.1667. Found: 400.1673.

Provenance & Evidence