Trifluoroacetic acid methylene chloride → HCID 178500078, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (E)-tert-butyl 4-(3-(3-methoxy-3-oxoprop-1-enyl)-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (380 mg, 0.65 mmol) in 25% TFA/CH2Cl2 was stirred at room temperature. Next, the solvent was removed, and the residue was evaporated from toluene (2×30 mL). Neat TFA (10 mL) was added to the resulting residue and heated at 60° C. for 4 hours. TFA was removed in vacuo, and the residue was evaporated from toluene (2×10 mL). 2M HCl in ether (5 mL) was added to the residue, and the mixture was sonicated for a few minutes. The solid formed was filtered, washed with ether (3×10 mL) and dried under high vacuum for 6 hours to provide (E)-methyl 3-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl)acrylate hydrochloride salt (300 mg, 106% yield) as a solid. LCMS (APCI+) m/z 364.1 (M+H)+, Retention time=2.61 minutes.

Provenance & Evidence