Sulfuric Acid → HCID 44546064, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 78, prepared according to the method described in US 2008/0319012 A1) (130 mg, 0.31 mmol) in acetic acid (3 mL) was added conc. H2SO4 (0.7 mL) and the mixture was stirred at 100° C. After 2 hours, more conc. H2SO4 (0.2 mL) was added and the mixture was stirred at 100° C. for 1 hour. Then the reaction mixture was cooled to room temperature, diluted with H2O (10 mL) in the ice bath, and neutralized by addition of NH4OH solution to pH 7. The mixture was extracted with CH2Cl2 (3 times) and then the organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:20 (v/v) to 1:10 (v/v)) to afford the solid, which was recrystallized from CH2Cl2/MeOH/Et2O to give the title compound (131.6 mg, 68%). 1H NMR (300 MHz, CD3OD) δ 2.53 (3H, s), 4.23 (2H, s), 7.16-7.23 (3H, m), 7.54-7.59 (2H, m), 7.84 (1H, dd), 8.04 (2H, bs), 8.25 (1H, bs), 8.85 (2H, dd). MS (ESI) m/z 439 (MH+).

Provenance & Evidence