Hydroxylamine → HCID 75952218, compound

Participants

Reaction Conditions

Reaction Steps

Hydroxylamine (16.3 M solution in water, 0.3 mL, 4.8 mmol) was added to 5-(5-bromo-1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (7 mg, 0.018 mmol) in MeOH (0.6 mL) and the reaction was stirred at 150° C. for 20 min in the microwave. The crude reaction was purified on preparative HPLC to give E9 5-(5-bromo-1,3-dimethyl-1H-pyrrol-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-N′-hydroxy-3-methyl-1H-pyrazole-4-carboximidamide (2.47 mg, 33%). 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: 422.00, 424.00 (M+H), 420.09, 422.07 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.11 (s, 1H), 7.20 (t, 1H, J=8.8 Hz), 6.86 (s, 1H), 6.70 (m, 1H), 6.62 (dd, 1H, J=2.6, 11.9 Hz), 3.41 (s, 3H), 2.39 (s, 3H) and 1.66 (s, 3H).

Provenance & Evidence