Triethylamine → N-(1-benzyl-3-cyclopropyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

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Reaction Steps

To a magnetically stirred, ice cooled, suspension of 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (29.5 mg, 0.125 mmol) (prepared as in Example 1, steps A-D) in dichloromethane (1 mL) was added N,N-dimethylformamide (5 μL) followed by oxalyl chloride (79.7 μL, 0.159 mmol; 2M solution in dichloromethane). The mixture was stirred in a sealed vial and allowed to warm to ambient temperature. The vial was occasionally vented to allow gases to evolve. After 30 minutes a solution of 1-benzyl-3-cyclopropyl-1H-indazol-4-amine (35.0 mg, 0.133 mmol) in dichloromethane was added followed by triethylamine (27.8 μL; 0.199 mmol). The mixture was stirred for 24 hours and then concentrated under reduced pressure. The material was purified by preparative thin layer chromatography, eluting with 10% methanol in dichloromethane. Further purification was carried out eluting with hexane/ethyl acetate (3:1). The desired band was isolated and concentrated to give N-(1-benzyl-3-cyclopropyl-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (17.5 mg). MS (APCI), positive scan, m/z=482.3 (M+H).

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