Ammonium Chloride → N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-hydroxybutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

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To a solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(3-oxobutyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.156 mmol) in MeOH (5 mL) was added NaBH4 (30 mg, 0.78 mmol) at 0° C. The mixture was warmed at room temperature and stirred for 1 hour. Aqueous NH4Cl solution was added to the mixture and product extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was used in the next step without purification. MS: (M+H)+=715.

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