1-Pyrrolidineethanamine → HCID 86732788, compound

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Reaction Steps

To a solution of 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (Example 16f) (5 g, 8.68 mmol) in N,N-Dimethylformamide (DMF) (75 mL) was added HATU (3.96 g, 10.42 mmol) and DIPEA (4.55 mL, 26.1 mmol), the resulting mixture was stirred at r.t. for 15 min. Then 2-(pyrrolidin-1-yl)ethanamine (1.502 mL, 9.55 mmol) was added and the resulting mixture was stirred at r.t. for 1 h. The mixture was concentrated and partitioned between water and DCM. The organic layer was separated and washed with water (2×), sat. NaHCO3 (aq.) and brine. The organic solution was dried over Na2SO4, and concentrated. The residue was purified by automated silica gel chromatography (CombiFlash Rf) eluting with MeOH/DCM (0-25%), followed by reverse phase chromatography (CombiFlash Rf) eluting with ACN/water (0-100%) to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydroquinoline-3-carboxamide (3.6 g, 5.81 mmol, 66.9% yield) as a white solid. LCMS: (M+H)+: 620.5

Provenance & Evidence