N-(2-Aminoethyl)ethyleneurea → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (10 mg, 0.028 mmol) described in example 92 and 1-(2-aminoethyl)-2-imidazolidinone (47 mg, 0.364 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-N-[2-(2-oxo-1-imidazolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (12 mg, 98% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.33 (br s, 1 H), 8.54 (s, 1 H), 7.37 (s, 1 H), 7.16-7.13 (m, 2 H), 7.03-6.99 (m, 2 H), 4.38 (s, 1 H), 4.12 (s, 2 H), 3.62 (m, 2 H), 3.56-3.53 (m, 5 H), 3.45-3.39 (m, 4 H); HRMS m/z calcd for C22H23N5O4F: 440.1734 Found: 440.1732.

Provenance & Evidence