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

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Reaction Steps

A mixture of 2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (100 mg, 0.28 mmol), 2-methylpropan-2-amine (20 mg, 0.28 mmol), HOBt (149 mg, 1.12 mmol), EDCI (211 mg, 1.12 mmol) and triethylamine (133 mg, 1.12 mmol) in dichloromethane (15 mL) was stirred at room temperature for 15 hours, then water (30 mL) was added, product extracted with dichloromethane (3×30 mL), the combined organic layers were concentrated and the residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with petroleum ether/ethyl acetate=10:1) to give N-tert-butyl-2-(1-methyl-5-(trifluoromethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (18 mg, 15.6%) as an orange solid. LCMS: (M+H)+=417; 1H NMR (300 MHz, DMSO): δ 12.89 (s, 1H), 9.06 (s, 1H), 8.71 (s, 1H), 8.44 (s, 1H), 8.05 (d, 1H, J=9.0 Hz), 7.93 (s, 1H), 7.84 (d, 1H, J=9.0 Hz), 4.28 (s, 3H), 1.47 (s, 9H).

Provenance & Evidence