Hydrochloric Acid → 1-[4-(3-Phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine

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To a solution of {1-[4-(3-phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (84 mg, 0.16 mmol) in MeOH (0.8 mL) and CH2Cl2 (1.3 mL) was added a 4 molar solution of HCl in dioxane (0.8 mL, 3.1 mmol, 20 equiv) and the resulting solution was stirred at room temperature for 18 h with monitoring by UPLC-MS and the resulting solution was concentrated under reduced pressure. The remaining material (84 mg) was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 1 min., gradient to 95% CH2Cl2: 5% MeOH over 10 min.; 95% CH2Cl2: 5% MeOH for 5.2 min.). The resulting partially purified material (48 mg) was triturated with diisopropyl ether to give 1-[4-(3-phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (18 mg, 24%). The resulting diisopropyl ether solution was concentrated under reduced pressure. The remaining material was triturated with diisopropyl ether to give 1-[4-(3-phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (20 mg, 30%, 54% total):

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