Imidazole → 1-Ethyl-3-[7-pyridin-3-yl-5-(pyrrolidine-1-carbonyl)-imidazo[1,2-a]pyridin-2-yl]-urea

Participants

Reaction Conditions

Reaction Steps

A dry mixture of imidazole (2 g) and 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (which may be produced as described in Example 16, Step 1) (0.160 g, 0.452 mmol) was heated until it became a homogeneous melt. It was then allowed to cool and solidify. To the solid was added pyrrolidine (0.1 mL) and the mixture was heated until it became a homogeneous melt, then allowed to cool to 23° C. Additional pyrrolidine (0.1 mL) was added and the reaction was heated at melt temperature for 30 sec. The reaction was cooled to RT and allowed to solidify. The solid was partitioned between water and EtOAc and the aqueous layer was extracted EtOAc (3×15 mL). The combined organic layers were then washed with brine and dried over sodium sulfate. Evaporation in vacuo gave a solid that was purified by silica gel chromatography (gradient elution 2-30% isopropanol/dichloromethane) to give the desired product. MS (APCI+)=380.1

Provenance & Evidence