Hydrochloric Acid → C-[6-(2,4-Dichloro-phenyl)-8-methoxy-3-morpholin-4-yl-imidazo[1,2-a]pyridin-7yl]-methylamine

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Reaction Steps

A mixture of 8-chloro-6-(2,4-dichloro-phenyl)-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile (20 mg, 0.05 mmol, prepared according to Example 30, Step 16.1) and NaOMe (8.2 mg, 0.15 mmol) in MeOH (0.5 mL) was refluxed and stirred for 1 h. The reaction mixture was cooled to RT, poured into water (20 ml) and extracted with DCM (3×10 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated. The remaining residue was dissolved in THF and a BH3.THF complex (1.0 M solution in THF, 0.2 mL, 0.2 mmol) followed by a 4M HCl solution in dioxane (2 drops) were added. The reaction mixture was stirred and refluxed for 2 h30, then cooled to 0° C. (ice bath) and poured into MeOH. The resulting solution was evaporated to dryness and the remaining residue was purified by reverse phase prep-HPLC (Waters system) to give the title compound (2TFA salt, 3.3 mg, 0.005 mmol, 9% for 2 steps). MS: 407 [M+1]+; HPLC: AtRet=1.09.

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