Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-pyridinecarboxamide

Participants

Reaction Steps

To a solution of 5-methyl-2-pyridinecarboxylic acid (55 mg, 0.40 mmol, available from Synchem OHG) in DMF (2 ml) was added HATU (150 mg, 0.40 mmol) and DIPEA (0.211 ml, 1.21 mmol). The mixture was stirred at room temperature for 20 mins then 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.20 mmol) was added and the mixture stirred at room temperature for 18 h. The reaction mixture was added to the top of a 2 g aminopropyl cartridge that had been preconditioned with MeOH. The reaction mixture remained on the cartridges for 3 h before being eluted with MeOH. The solvent was removed in vacuo to give a crude residue that was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method C). The product was loaded onto a 1 g aminopropyl column, eluted with DCM/MeOH (1:1) and the solvent removed under a stream of nitrogen to give the title compound (20 mg) as a cream solid.

Provenance & Evidence