Methylamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-methyl-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 methylamine (0.11 mL of a 8M solution in ethanol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (10 mg, 17% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 9.97 (br s, 1 H), 8.58 (s, 1 H), 7.46 (s, 1 H), 7.17-7.13 (m, 2 H), 7.04-6.99 (m, 2 H), 4.32 (m, 2 H), 4.13 (s, 2 H), 3.49 (m, 2 H), 3.21 (m, 1 H), 3.01 (d, J=4.8 Hz, 3 H), 1.83 (m, 2 H); HRMS m/z calcd for C20H21N3O4F: 386.1516. Found: 386.1517.

Provenance & Evidence