Sodium Hydroxide → HCID 89783358, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel (80 mL) was charged with ethyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-5-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (284a) (0.41 g, 0.81 mmol) and LiOH monohydrate (Sigma-Aldrich) (342 mg, 8.16 mmol) in 1,4-Dioxane (12 mL) and water (10 mL). The reaction mixture was stirred and heated in a CEM Voyager Microwave (Large-Scale Unit) at 120° C. for 35 min (100 watts, Powermax feature off). This material was transferred to a 150-mL round-bottomed flask for next step in the reaction. m/z (ESI, +ve) 470 (M+H). To the mixture from step 1, was added 4 M HCl/1,4-dioxane (Sigma-Aldrich) until pH 2-3. The mixture was stirred at RT for 4 h. The mixture was neutralized with 5 N NaOH (pH 7). The precipitate was collected by filtration and the solids were washed with hexanes. This gave 2-(1-aminoethyl)-5-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid (284b; 285 mg, 0.77 mmol, 95% yield) as light yellow solid. m/z (ESI, +ve) 353 (M-NH2)′.

Provenance & Evidence