N~1~-[3-(4-Methylpiperazin-1-yl)propyl]benzene-1,4-diamine → HCID 178426957, compound

Participants

Reaction Conditions

Reaction Steps

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 100 mg, 0.249 mmol) and THF (2.5 mL). To the resulting solution was added N-[3-(4-Methyl-piperazin-1-yl)-propyl]-benzene-1,4-diamine (prepared below, 86.2 mg, 0.347 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature and then diluted with Hexanes (˜40 mL). The black precipitate that formed was removed by filtration and the filtrate was concentrated in vacuo. The crude residue was dissolved in EtOAc (˜5 mL) and triturated with Hexane (˜50 mL) to give a yellow precipitate. The precipitate was filtered and washed with 0° C. i-prOH (˜5 mL) yielding 51% (0.0802 g, 0.127 mmol) of the title compound.

Provenance & Evidence