Hydrochloric Acid → HCID 136350243, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (9.1 mg, 0.029 mmol), hydroxylamine hydrochloride (54.9 mg, 0.79 mmol) and pyridine (69 μL, 0.85 mmol) in dry EtOH (1 mL) was heated at 100° C. for 3 minutes in the microwave. 1 mL 2 M HCl and 5 mL DCM were added and the phases were separated. The organic phase was filtered through a phase separator and concentrated to give a raw product, that was dissolved in DCM (0.5 mL). BF3.Me2S (1 M solution in DCM, 0.5 mL, 0.5 mmol) was added and the mixture was stirred at room temperature over night. Methanol was added to quenched the reaction and the mixture was purified on preparative HPLC to give E12 4-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde oxime (3.0 mg, 0.01 mmol, 32%). Identification of the title compound by 1H-NMR showed that the oxime product was a single isomer, but did not confirm whether the (E) or (Z) oxime isomer had been obtained. ES/MS m/z: 313.22 (M+H), 311.21 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.92 (s, 1H), 7.31 (m, 2H), 6.79 (m, 2H), 4.08 (s, 3H), 2.15 (s, 3H) and 1.86 (s, 3H).

Provenance & Evidence