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

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Reaction Steps

To a solution of {1-[4-(3-phenyl-7-vinyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (77 mg, 0.17 mmol) in MeOH (0.7 mL) and CH2Cl2 (1.1 mL) was added a 4 molar solution of HCl in dioxane (0.8 mL, 3.3 mmol, 20 equiv) and the resulting solution was stirred at room temperature for 18 h with monitoring by UPLC-MS. The resulting material was concentrated under reduced pressure. The remaining material (82 mg) was purified using MPLC (Isolute Flash NH2 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.) to give partially purified material, which was further purified using preparative HPLC (Waters Autopurification System equipped with pump 254, Sample Manager 2767, CFO, DAD 2996, ELSD 2424 and SQD 3001 using a XBridge C18 5 uM 100×30 mm column; 70% water with 0.2% NH3/30% acetonitrile 1 min., gradient to 30% water with 0.2% NH3/70% acetonitrile over 7 min.) to give 1-[4-(3-phenyl-7-vinyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (7 mg, 11%):

Provenance & Evidence