1-Pyrrolidineethanamine → HCID 86732741, compound

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Reaction Steps

To a suspension of 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (Example 8c) (2.5 g, 5.10 mmol) in dichloromethane (50 mL) at room temperature was added thionyl chloride (0.446 mL, 6.12 mmol), and the mixture was heated to reflux for 1 h. After cooling to room temperature the mixture was added dropwise to a solution of 2-(pyrrolidin-1-yl)ethanamine (0.711 mL, 5.61 mmol) and triethylamine (1.066 mL, 7.65 mmol) in dichloromethane (50.0 mL) in an ice bath. The resulting mixture was then allowed to warm up to room temperature, and stirred for another 0.5 h. LCMS indicated completion of the reaction. The mixture was concentrated in vacuo, and the residue was purified twice by automatic silica gel column chromatography (Combiflash RF), eluting with a mixture of [dichloromethane/methanol/ammonium hydroxide (80:20:2)]/dichloromethane (0-50%) to afford 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydrocinnoline-3-carboxamide (2.2 g, 3.75 mmol, 73.6% yield) as a light yellow solid. LCMS: (M+H)+: 587.3.

Provenance & Evidence