Ethyl 6-(2-(bis(tert-butoxycarbonyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate → Ethyl 6-(2-aminothiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate

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Reaction Steps

A solution of ethyl 6-(2-(bis(tert-butoxycarbonyl)amino)thiazol-5-yl)-8-phenyl-imidazo[1,2-a]pyridine-2-carboxylate (28 mg) in 3 ml of TFA was stirred at room temperature for 2 hours. The Solvent was evaporated and the residue made basic with NH4OH/MeOH/CH2Cl2 (1:9:90) solution, and then evaporated to dryness. The residue was purified by column chromatography on silica gel using ethyl acetate as eluent to give 7 mg of Ethyl 6-(2-aminothiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate as a white solid. LCMS (Conditions C): 2.53 min (RT); (M+H)+=365.28 (100%). 1H NMR, 400 MHz, DMSO: δ 8.56 (m, 2 H), 8.11 (m, 2 H), 7.81 (s, 1H), 7.65 (s, 1H), 7.56-7.47 (m, 3 H), 7.32 (bs, 2 H), 4.33 (q, J=7.1 Hz, 2 H), 1.31 (t, J=7.0 Hz, 3 H).

Provenance & Evidence