N-(2-aminoethyl)-N'-methylthiourea → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-(2-{[(methylamino)carbonothioyl]amino}ethyl)-2-oxo-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 N-(2-aminoethyl)-N′-methylthiourea (48 mg, 0.364 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-(2-{[(methylamino)carbonothioyl]amino}ethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide(4 mg, 33% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.55 (br s, 1 H), 8.56 (s, 1 H), 7.40 (s, 1 H), 7.24-7.15 (m, 2 H), 7.05-7.00 (m, 2 H), 6.79 (br s, 1 H), 6.19 (br s, 1 H), 4.14 (s, 2 H), 3.75-3.70 (m, 4 H), 3.56 (s, 3 H), 2.95 (s, 3 H); HRMS m/z calcd for C21H23N5O3FS: 444.1506 Found: 444.1532.

Provenance & Evidence