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

Participants

Reaction Steps

To a solution of 6-(1-piperidinylmethyl)-2-pyridinecarboxylic acid (33 mg, 0.15 mmol) in DMF (0.6 ml) was added O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (57 mg, 0.15 mmol) and DIPEA (0.052 ml) and the mixture was stirred for 5 mins at room temperature. 6-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (33 mg, 0.10 mmol) was added and the mixture was stirred for 3 h and then overnight. The mixture was then treated with saturated sodium bicarbonate solution (10 ml) and extracted with dichloromethane (3×10 ml). The extracts were passed through a hydrophobic frit and blown to dryness under a stream of nitrogen. The crude product was dissolved in methanol (2 ml) and hydrochloric acid (5M, 2-3 drops) were added. The solution was shaken for 2 h then blown to dryness under a stream of nitrogen then purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound (17 mg).

Provenance & Evidence