Triethylamine → 7-(3-Amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid

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Reaction Steps

A mixture of 0.70 g (2.50 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, 0.56 g (3.00 mmol) of 3-(t-butoxycarbonyl) aminopyrrolidine, 0.76 g (7.52 mmol) of triethylamine, and 25 mL of acetonitrile was refluxed for 4.5 hours, then stirred at room temperature overnight. The solids were collected by filtration and washed with acetonitrile and ether. The crude product was dissolved in 20 mL of 6N hydrochloric acid and 20 mL of acetic acid and was stirred at room temperature for 3 hours. The solution was concentrated to an oil which was triturated with 2:1 ether:isopropanol. The solids were removed by filtration, washed with ether, and dried to give 0.95 g of the title compound as the hydrochloride salt, mp>300° C.

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