1-Pyrrolidineethanamine → HCID 86732810, compound

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Reaction Steps

To a solution of 1-ethyl-5-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydro quinoline-3-carboxylic acid (Example 36h) (5 g, 9.85 mmol) in N,N-Dimethylformamide (DMF) (5 mL) was added HATU (5.62 g, 14.78 mmol) and DIPEA (5.16 mL, 29.6 mmol), the resulting mixture was stirred at r.t. for 30 min. Then 2-(pyrrolidin-1-yl)ethanamine (1.861 mL, 14.78 mmol) was added and the resulting mixture was stirred at r.t. overnight. The mixture was concentrated and the residue was purified by normal phase automatic silica column chromatography (Combiflash RF) eluting with MeOH/DCM (0-20%). The product was further purified by reverse phase automatic chromatography (Combinflash RF), using a 150 g golden C18 column and eluting with acetonitrile/Water (0%-100%) to afford 1-ethyl-5-fluoro-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydroquinoline-3-carboxamide (3.8 g, 6.29 mmol, 63.9% yield) as pale yellow solid. LCMS: (M+H)+: 604.4.

Provenance & Evidence