Acetic Acid → HCID 9880611, compound

Participants

Reaction Steps

To a solution of 47 mg (0.2 mmol) of 1-[1-(3-chlorophenyl)-5-methyl-1H-pyrazol-4-yl]ethan-1-one (commercially available) in 2 mL of THF was added successively 0.4 mL (0.4 mmol) of 1M KOtBu in THF and 54 μL (0.4 mmol) of diethyl oxalate. The mixture was stirred at room temperature overnight, quenched with water, and diluted with ethyl acetate. The solution was washed successively with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was diluted with 2 mL of ethanol, and 15 mL (0.3 mmol) of hydrazine monohydrate was added followed by 15 mL (0.3 mmol) of acetic acid. The mixture was stirred at room temperature for 2 hours, and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC to afford 8 mg of the title compound as the trifluoroacetic acid salt. MS m/e expected M+1 333.18, found m/e 333.01. 1H NMR (DMSO-d6) δ 14.0 (s, 0.45H), 13.8 (s, 0.55H), 8.05 (s, 1H), 7.75 (s, 1H), 7.55 (m, 3H), 7.1 (br s, 0.45H), 6.8 (br s, 0.55H), 4.3 (br s, 2H), 2.65 (br s, 1.4H), 2.4 (br s, 1.6H), 1.3 (t, 3H).

Provenance & Evidence