Hydrochloric Acid → 5-(6-fluoro-2-methyl-3-((1-methyl-cyclopropyl)amino)quinoxalin-5-yl)-2-methyl-1H-pyrrole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 5-(6-fluoro-2-methyl-3-((1-methyl-cyclopropyl)amino)quinoxalin-5-yl)-2-methyl-1H-pyrrole-3-carboxylate (417b) (0.555 g, 1.451 mmol), LiOH monohydrate (Sigma Aldrich, 365 mg, 8.71 mmol) in water (9 mL) and dioxane (18.00 mL) was heated to 80° C. overnight. Reaction mixture was then heated to 105° C. for an additional 4 h. Mixture was cooled back to RT and quenched with 4 M HCl in 1,4-dioxane (Sigma Aldrich, 2.177 mL, 8.71 mmol). Volatile solvents were removed by rotovap. The residue was loaded onto a silica gel samplet. Purification by Biotage (0-100% EtOAc/hexanes) produced 5-(6-fluoro-2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-2-methyl-1H-pyrrole-3-carboxylic acid (417c) (78 mg, 0.220 mmol, 15% yield). m/z (ESI, +ve) 355.0 (M+H).

Provenance & Evidence