Hydrochloric Acid → HCID 89783657, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylate (283d) (0.38 g, 0.76 mmol) and LiOH monohydrate (Fluka/Aldrich) (191 mg, 4.56 mmol) in 1,4-Dioxane (7 mL)/Water (3.5 mL). The reaction mixture was stirred and heated in a Discover model microwave reactor (CEM, Matthews, N.C.) at 120° C. for 20 min (100 watts, Powermax feature off). This material was transferred to a 150-mL round-bottomed flask and added 4 M HCl in 1,4-dioxane (Aldrich) until pH 2-3. The mixture was stirred at RT for 2 h. The mixture was neutralized with 5 N NaOH (pH 7), then concentrated under reduced pressure to half of its volume. The residue was diluted with hexanes and placed into a sonicator for 30 sec. The precipitated solid was collected by filtration and washed with hexanes. This gave 2-(1-aminocyclopropyl)-5-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (283e) (0.30 g, 0.718 mmol, 95% yield) as a tan solid. 1H NMR (400 MHz, MeOH-d4) δ ppm 7.86 (m, 1H), 7.44 (m, 1H), 7.34 (s, 1H), 2.68 (s, 3H), 1.56 (m, 4H), 1.14 (d, 2H), 0.91 (s, 2H). m/z (ESI, +ve) 383 (M+H).

Provenance & Evidence