Hydrochloric Acid → 2-methyl-4-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]-1H-imidazol-1-amine

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Reaction Steps

Aqueous hydrochloric acid (1 N, 7.0 mL) was added to a solution of N-{2-methyl-4-[1-methyl-5-(4-methylphenyl)-1H-pyrazol-4-yl]-1H-imidazol-1-yl}acetamide (236 mg, 0.763 mmol) in methanol (1.0 mL), and the mixture was heated at reflux for 30 minutes. Additional 1 N aqueous hydrochloric acid (2.0 mL) was added, and heating was continued for an additional 30 minutes. After cooling, the solution was basified with 1 N aqueous sodium hydroxide solution, and the mixture was extracted twice with ethyl acetate containing 1% methanol. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the product as a yellow solid. Yield: 148.5 mg, 0.5555 mmol, 73%. LCMS m/z 268.5 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.39 (s, 3H), 2.45 (br s, 3H), 3.70 (s, 3H), 4.45 (br s, 2H), 6.26 (s, 1H), 7.24-7.32 (m, 4H, assumed; partially obscured by solvent peak), 7.97 (s, 1H).

Provenance & Evidence