Methanamine, N-methoxy-, hydrochloride (1:1) → 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide

Participants

Reaction Steps

A mixture of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester (0.72 g, 1.6 mmol, 1 equiv) and methylmethoxyamine hydrochloride (0.16 g, 1 equiv) in 2 mL of toluene was treated with AlMe3 (0.5 M in toluene, 3.5 mL, 1.1 equiv) at rt for 1 h. The reaction was quenched by slow addition of saturated aqueous solution of sodium potassium tartrate. The organic layer was dried over sodium sulfate, filtered and evaporated to give crude 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3carboxylic acid methoxy-methyl-amide.

Provenance & Evidence