Tert-Butylamine → 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-N-tert-butyl-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

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Reaction Steps

A mixture of 2-(5-(4-Amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (100 mg, 0.15 mmol), tert-butylamine (0.05 mL, 0.45 mmol) and HATU (68.4 mg, 0.18 mmol) in 10 mL of dry THF was stirred for 4 hours at room temperature. The reaction mixture was evaporated to dryness, the residue was suspended in 50 mL of 0.5 N HCl, and product extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to afford 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-N-tert-butyl-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (88 mg, 62%) as dark oil, material used in the next step without further purification. LCMS: (M+H)+=706.

Provenance & Evidence