Triethylamine → 1,6-Dihydro-1-[2-(6-methyl-3-pyridinylcarbonylamino)ethyl]-6-oxo-3-pyridinecarboxylic acid methyl ester

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Reaction Steps

1-(2-aminoethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid methyl ester (0.50 g, 2.55 mmol) was coupled with 6-methyl-3-pyridinecarboxylic acid (0.42 g, 3.1 mmol)in dimethylformamide (42.5 ml) with triethylamine (1.80 ml, 12.75 mmol) and propylphosphonic acid anhydride (0.90 ml, added as a 0.90 ml ethyl acetate solution). After 72 hours, dichloromethane and aqueous sodium bicarbonate were added. The layers were separated and the organic layer washed with brine and dried (Na2SO4). Filtration, concentration, and purification by medium pressure liquid chromotography (silica gel, 4-6% methanol/dichloromethane) gave the desired product, MP: 184°-185° C.

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