Ethylene Glycol → 4-[4-[(6,8-Dichloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 6,8-dichloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 19, Step 1; 0.301 g), 4-(piperazin-1-yl)benzamide (Example 3, Step 1; 0.2916 g), triethylamine (Aldrich; 0.21 mL), and ethylene glycol (2 mL) is stirred for 1 h at 80-85° C. The mixture is then allowed to cool and water is added. The solids are collected, washed with water and hexane, and dried under reduced pressure. The solid is then adsorbed onto silica gel and chromatographed using methanol/dichloromethane (8/92). The appropriate fractions are combined and concentrated and the residue is crystallized from dichloromethane/methanol to give 0.2938 g of the title compound; mp 234-235° C.; MS m/z 403,405; IR (mineral oil) 1606, 1668, 1392, 1522, 1241 cm-1 ; 1H NMR (CDCl3) δ2.74, 3.35, 3.83, 6.89, 7.27, 7.63, 7.72, 8.10.

Provenance & Evidence