Triethylamine → 5-Amino-7-[3-(1-aminocyclobutyl)-1-pyrrolidinyl]-6,8-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

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Reaction Steps

A 242 mg (1.00 mmol) portion of 3-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine (fr.2) was suspended in 10.0 ml of acetonitrile to which was subsequently added 212 mg (0.67 mmol) of 5-amino-6,7,8-trifluoro-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 1.40 ml (6.70 mmol) of triethylamine, followed by overnight heating under reflux. After evaporation of the solvent, the resulting residue was mixed with chloroform, washed with water, 10% citric acid aqueous solution and saturated brine in that order, and then dried over anhydrous sodium sulfate, followed by evaporation of the solvent. Thereto was added 2 ml of concentrated hydrochloric acid, followed by 2 hours of stirring at room temperature. The reaction solution was mixed with 10 ml of water, washed with chloroform and then neutralized with sodium hydroxide aqueous solution. This was extracted with chloroform and dried over sodium sulfate, and then the solvent was evaporated. Thereafter, the resulting residue was recrystallized from ethanol-diisopropyl ether to yield 292 mg (37%) of the title compound as a yellow solid.

Provenance & Evidence