2-(1-((4-benzylmorpholin-2-yl)methyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide → N-tert-butyl-2-(5-(difluoromethoxy)-1-(morpholin-2-ylmethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

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To a stirred solution of 2-(1-((4-benzylmorpholin-2-yl)methyl)-5-(difluoromethoxy)-1H-indazol-3-yl)-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (see Example 340, 130 mg, 181 μmol) in ethyl acetate (2 mL) and methanol (1 mL) was added palladium on carbon (19.2 mg) and the mixture hydrogenated using a balloon filled with hydrogen gas. After stirring at room temperature for 15 h, the mixture was transferred to a Parr hydrogenator and shaken under 40 psi for 1 h. The mixture was filtered, concentrated in vacuo and then purified by chromatography (silica, 24 g Analogix column, 0-100% ethyl acetate in hexanes followed by 5% methanol in ethyl acetate) to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(morpholin-2-ylmethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.10 g 88%). MS (M+H)+=630.

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