Hydrochloric Acid → HCID 66665927, compound

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Reaction Steps

To a solution of {1-[4-(3-phenyl-7-pyridin-4-yl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (60 mg, 0.12 mmol) in MeOH (0.5 mL) and CH2Cl2 (0.7 mL) was added a 4 molar solution of HCl in dioxane (0.6 mL, 2.3 mmol, 20 equiv) and the resulting solution was stirred at room temperature for 12 h. The resulting solution was added to ice water, and the resulting mixture was extracted with CH2Cl2 (3×25 mL). The combined organic phases were dried (Na2SO4 anh), and concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 4 min., gradient to 95% CH2Cl2: 5% MeOH over 1 min.; 95% CH2Cl2: 5% MeOH for 2.5 min., gradient to 90% CH2Cl2: 10% MeOH over 1 min., 90% CH2Cl2: 10% MeOH for 2.5 min., gradient to 80% CH2Cl2: 20% MeOH over 1.5 min., 80% CH2Cl2: 20% MeOH for 0.8 min., gradient to 74% CH2Cl2: 26% MeOH over 2.2 min., gradient to 70% CH2Cl2: 30% MeOH over 1.8 min., 70% CH2Cl2: 30% MeOH for 7.4 min.) to give 1-[4-(3-phenyl-7-pyridin-4-yl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (40 mg, 83%): UPLC-MS (Method 2): RT=1.22 min; m/z (rel intensity) 417 (700, (M+H)+), 833 (40, (2M+H)+).

Provenance & Evidence