Diisopropylethylamine → 5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

In a 25 mL flask were combined 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 0.45 mmol), 1-benzyl-4,4-dimethylpiperidin-3-amine (147 mg, 0.68 mmol), and HATU (188 mg, 0.50 mmol). Then added DMF (3 mL) followed by N,N-diisopropylethylamine (0.24 mL 1.35 mmol). The yellow reaction mixture was stirred at room temperature for 3 h then quenched with H2O and extracted with EtOAc (3×). The combined organics were washed with H2O (3×), dried over MgSO4 and concentrated. The crude residue was purified by SiO2 chromatography (30% to 80% EtOAc/hexanes) to afford 197 mg (82%) of N-(1-benzyl-4,4-dimethylpiperidin-3-yl)-2-cyclopropyl-5-(2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a white foam.

Provenance & Evidence