1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-ylmethyl)-amide

Beteiligte Stoffe

Reaktionsschritte

In a 50 mL round-bottomed flask, 1-benzyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (21 mg, 0.93 mmol), 1-(3-dimethylaminopropyl-3-ethylcarbodiimide (23.0 mg, 0.148 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (20.0 mg, 0.148 mmol) and N,N-diisopropylethylamine were combined with methylene chloride (5 mL). The reaction mixture was stirred at room temperature for 10 min. After this time, 3-(aminomethyl)-2-(oxazol-2-yl)-1-phenyl-1,8-naphthyridin-4(1H)-one (intermediate B) was added. The reaction mixture was stirred at room temperature over the weekend. The reaction mixture was partitioned between methylene chloride and water. The organic phase was dried over sodium sulfate, then filtered and concentrated. The crude product was purified using flash chromatography (Isco, 0% ethyl acetate-hexanes ramped to 70% ethyl acetate-hexanes) to afford 1-Benzyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-ylmethyl)-amide as a light brown powder (12 mg). MS calcd. for C31H24N5O4 [(M+H)+] 530.2, obsd. 530.3

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