4-(4-Methylpiperazin-1-yl)aniline → 4-chloro-1-methyl-N-[3-[3-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-2-oxo-1H-indole-6-carbonyl]phenyl]pyrazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

A small screw cap test tube was charged with 4-Chloro-2-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (prepared below, 100 mg, 0.240 mmol) and THF (2 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (50.53 mg, 0.264 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was dissolved in EtOAc. The resulting solution was diluted with Hexanes to initiate the precipitation of the product. The solid precipitate that formed was filtered then washed with ˜1 mL of i-prOH yielding 32% (45 mg, 0.076 mmol) of the title compound.

Provenance & Evidence