Sulfuric Acid → HCID 59160544, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 76) (300 mg, 0.715 mmol) was treated with conc. H2SO4 (2.4 mL) and H2O (0.8 ml) and the mixture was stirred at 120° C. for 10 hours. The reaction mixture was cooled to room temperature and basified to pH 9-10 with 5N NaOH solution in the ice bath. The solution was extracted with CH2Cl2 (5 mL, 3 times), and then the aqueous layer was acidified to pH 4 with 2N HCl solution. The precipitate was filtered, washed with H2O, and dried under vacuum for overnight to afford the title compound (213 mg, 49%). (300 MHz, CDCl3+CD3OD) δ 2.48 (3H, s), 4.15 (2H, s), 6.97 (1H, d), 7.05 (1H, dd), 7.14 (1H, d), 7.35-7.42 (2H, m), 7.47-7.52 (1H, m), 7.83 (1H, dd), 7.90 (1H, dd), 8.01 (1H, d), 8.08 (1H, d), 8.16 (1H, dd), 8.80 (1H, dd). MS (ESI) m/z 439 (MH+).

Provenance & Evidence