Acetohydroxamic Acid → 5-(4-amino-1-isopropyl-1H-pyrazolo[4,3-c]pyridin-3-yl)benzo[d]isoxazol-3-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(4-amino-1-isopropyl-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-fluorobenzonitrile (304) (49 mg, 0.166 mmol), N-hydroxyacetamide (compound 305) (18.7 mg, 1.5 eq, 0.249 mmol) and t-BuOK (27.9 mg, 1.5 eq, 0.249 mmol) in DMF (4 mL) was stirred at 25° C. overnight. The mixture was concentrated in vacuo, brine (10 mL) was added and then extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine (10 mL), dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography eluting with a mixture of methanol in dichloromethane to afford the desired product, 5-(4-amino-1-isopropyl-1H-pyrazolo[4,3-c]pyridin-3-yl)benzo[d]isoxazol-3-amine (7) (28 mg, 55% yield) (compound 306) as a white solid. ESI-MS m/z: 309.35 [M+1]+.

Provenance & Evidence