4-(4-Methylpiperazin-1-yl)aniline → HCID 178426332, compound

Participants

Reaction Conditions

Reaction Steps

A small screw cap test tube was charged with 6-{3-[(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-amino]-benzoyl}-3-hydroxymethylene-1,3-dihydro-indol-2-one (prepared below, 0.045 g, 0.117 mmol) and THF (2 mL). To the resulting solution was added 4-(4-Methyl-piperazin-1-yl)-phenylamine (23 mg, 0.117 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature and the precipitate that formed was collected by filtration. The yellow solid was dissolved in 5 mL of a solvent mixture containing 98% EtOAc/2% i-prOH and washed with water (2×5 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was columned over silica (95/5, chloroform/Hexanes w/0.5% NEt3 to afford the title compound in 39% yield (26 mg, 0.045 mmol).

Provenance & Evidence