Cyclopropanesulfonamide → 8-Quinolinecarboxamide, N-(cyclopropylsulfonyl)-6-fluoro-1,2,3,4-tetrahydro-4,4-dimethyl-2-[3-(1-pyrrolidinyl)phenyl]-

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Reaction Steps

A mixture of 6-fluoro-4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (150 mg, 0.32 mmol), 1-3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (91 mg, 0.48 mmol), 4-dimethylaminopyridine (59 mg, 0.48 mmol), cyclopropane sulfonic acid amide (149 mg, 1.23 mmol) in dichloromethane (10 mL) was refluxed for 12 h. Removal of the solvent to afford the oil residue. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% formic acid in water) afforded cyclopropanesulfonic acid [6-fluoro-4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carbonyl]-amide (38.6 mg, 20%) as a light yellow solid: MS (ESI) M+1=472.3.

Provenance & Evidence