N-(2-Aminoethyl)ethyleneurea → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-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 1-(2-aminoethyl)-2-imidazolidinone (0.4 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (22 mg, 31% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.25 (br s, 1 H), 8.55 (s, 1 H), 7.46 (s, 1 H), 7.16-7.12 (m, 2 H), 7.03-7.12 (m, 2 H), 4.73 (br s, 1 H), 4.29 (br s, 2 H), 4.11 (s, 2 H), 3.64-3.39 (m, 10 H), 1.79 (m, 2 H); HRMS m/z calcd for C24H27N5O5F: 484.1996. Found: 484.1997.

Provenance & Evidence