Hydrochloric Acid → HCID 178423771, compound

Participants

Reaction Conditions

Reaction Steps

1-(Tetrahydro-2H-pyran-2-yl)-N-(1-(tetrahydro-2H-pyran-2-yl)-5-p-tolyl-1H-pyrazol-3-yl)-5-p-tolyl-1H-pyrazole-3-carboxamide (142 mg, 0.27 mmol) was suspended in anhydrous THF (10 mL) and borane dimethylsulfide complex (177 μL, 1.86 mmol) was added dropwise. The reaction mixture was stirred under reflux for 16 hrs. The reaction mixture was then cooled down to 0° C. and MeOH (500 μL) was added. The mixture was then stirred for 10 min. Concentrated hydrochloric acid (12 N) was added, until a pH<2 was obtained, and the resulting mixture was stirred under reflux for 16 hrs. The mixture was cooled to room temperature and the precipitate was filtered and added into an aqueous solution of sodium hydroxide (1M). The aqueous phase was extracted with DCM (3×10 mL) after drying the organic layers with Na2SO4, the solvent was evaporated. The residue was purified by chromatography on silica gel column (eluent: EtOAc); 5-p-tolyl-N-((5-p-tolyl-1H-pyrazol-3-yl)methyl)-1H-pyrazol-3-amine was obtained as a white solid.

Provenance & Evidence