Potassium Hydroxide → HCID 86621560, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl [2-(5-{[3-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}-2-thienyl)benzyl]carbamate (0.09 g, 0.14 mmol) in EtOH (1.7 mL) and water (0.75 mL) in a round-bottomed flask equipped with a reflux condenser was added hydroxylamine hydrochloride (0.58 g, 8.3 mmol) and potassium hydroxide (0.31 g, 5.6 mmol). The mixture was heated to 110° C. and allowed to stir vigorously for 5 h. The reaction was then cooled to rt and diluted with water. The aqueous solution was extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give tert-butyl [2-(5-{[3-(6-aminopyridin-3-yl)-5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]carbonyl}-2-thienyl)benzyl]carbamate as a white solid (0.04 g, 48%). LCMS: (FA) ES+ 570.6 (M+1).

Provenance & Evidence