Ethylene Glycol → HCID 54217619, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(chloromethyl)-7-methylimidazo[1,2-α]pyridine (Example 6, Step 1; 0.300 g), 4-(piperazin-1-yl)benzamide (Example 3, Step 1; 0.357 g), triethylamine (Aldrich; 0.26 mL), and ethylene glycol (2 mL) is stirred for 30 min at 80-85° C. Additional ethylene glycol (1 mL) is added and the mixture is stirred for another 1.5 h. Water (8 mL) is added to the cooled mixture and the resulting solid is collected and dried. This material is adsorbed to silica gel and chromatographed on silica gel using methanol/dichloromethane/ammonium hydroxide (8/92/0.5). The appropriate fractions are combined and concentrated and the residue is crystallized from ethyl acetate/methanol to give 0.211 g of the title compound; mp 217-218° C.; ms m/z 349; IR (mineral oil) 1608, 1662, 1239, 3393, 1520 cm-1 ; 1H NMR (CDCl3) δ2.39, 2.74. 3.35. 3.75, 6.60. 6.88, 7.32, 7.46, 7.70 7.95.

Provenance & Evidence