1-Pyrrolidineethanamine → HCID 86732822, compound

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Reaction Steps

To a solution of 1-ethyl-7,8-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (Example 44f) (7 g, 14.30 mmol) in N,N-Dimethylformamide (DMF) (50 mL) was added HATU (8.16 g, 21.45 mmol) and DIPEA (7.49 mL, 42.9 mmol), the resulting mixture was stirred at r.t. for 30 min. 2-(Pyrrolidin-1-yl)ethanamine (2.70 mL, 21.45 mmol) was added and the resulting mixture was stirred at r.t. for 3 h. The mixture was concentrated and the residue was purified by normal phase automatic silica column chromatography (Combiflash RF), eluting with MeOH/DCM (0-30%) to afford 1-ethyl-7,8-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydroquinoline-3-carboxamide (6.6 g, 11.27 mmol, 79% yield) as a pale yellow solid. LCMS: (M+H)+: 586.5.

Provenance & Evidence