Water → ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-((1-hydroxy-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (302b) (250 mg, 0.57 mmol) and 2-amino-2-methyl-1-propanol (Sigma-Aldrich) (0.11 mL, 1.13 mmol) in DMSO (2 mL) was heated at 70° C. for 18 h. The reaction mixture was cooled to RT and water and EtOAc was added. The layers were separated and the aq. layer was extracted with EtOAc (2×). The combined organic layers were washed with water and brine and dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by chromatography (0-100% EtOAc in hexanes) to provide ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(34(1-hydroxy-2-methylpropan-2-yl)amino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (302c) (208 mg, 0.41 mmol, 72% yield) as a yellow oil. m/z (ESI, +ve) 512.2 (M+H)+.

Provenance & Evidence