Piperidine → HCID 86732742, compound

Participants

Reaction Steps

To a suspension of 1-ethyl-3-(hydroxymethyl)-6,7-bis((4-methoxybenzyl)oxy)cinnolin-4(1H)-one (Example 8d) (2.13 g, 4.47 mmol) in Dichloromethane (DCM) (40 mL) in an ice bath under N2 was added TEA (1.495 mL, 10.73 mmol) followed by methanesulfonyl chloride (0.627 mL, 8.05 mmol) (white suspension turned into a light yellow clear solution). The mixture was stirred in an ice bath for 2 h, and then the above reaction mixture was added dropwise into a stirred solution of piperidine (1.195 mL, 12.07 mmol) in dichloromethane (DCM) (40.0 mL) at room temperature overnight. The reaction mixture was concentrated and purified through column chromatography eluting with dichloromethane and methanol/dichloromethane/ammonium hydroxide (from 0% to 100%) over 15 mins twice to afford 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(piperidin-1-ylmethyl)cinnolin-4(1H)-one (1.54 g, 2.55 mmol, 57.0% yield). LCMS (M+H)+: 544.0

Provenance & Evidence