1-(1-Methyl-1H-pyrazol-3-yl)ethan-1-one → HCID 178517415, compound

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Reaction Steps

This compound was generated exploiting General Procedure A-I from 1-(1-methyl-1H-pyrazol-3-yl)ethanone (1.67 g, 13.45 mmol) in the initial Claisen condensation, and using (2-fluorobenzyl)hydrazine hydrochloride (2.38 g, 13.45 mmol) in the pyrazole formation step (72%, two steps). The ester was then carried on to the corresponding amidine, again, as outlined in General Procedure A-I. The amidine (213 mg, 0.714 mmol) was cyclized via treatment with sodium 3-ethoxy-2-fluoro-3-oxoprop-1-en-1-olate (446 mg, 2.86 mmol) in ethanol (5.0 mL)—stirring at 90° C. for 14 hour. The solvent was removed in vacuo, and purification by silica gel chromatography (0-10% methanol in DCM) provided a mixture of the desired compound and a side-product. The mixture was then subjected to reverse-phase preparative HPLC which afforded Compound 92 (20 mg, 7.6% yield) as a white solid.

Provenance & Evidence