Ammonia → HCID 44540228, compound

Participants

Reaction Steps

A solution of 2-(1-pyrrolidinyl)-4-pyridinecarboxylic acid hydrochloride (38 mg, 0.16 mmol, available from Maybridge) in anhydrous THF (2 ml), was treated with 1-chloro-N,N,2-trimethyl-1-propen-1-amine (0.026 ml, 0.2 mmol, available from Acros) and stirred at room temperature under nitrogen for 2 h. The mixture was then treated with anhydrous DIPEA (0.131 ml, 0.75 mmol) followed by a solution of 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (50 mg, 0.15 mmol) in THF (2 ml). The mixture was stirred under nitrogen for a further 6 h. Solvents were removed by blow down under a stream of nitrogen and the residue was then dissolved in methanol (3 ml) and evaporated further in a vacuum centrifuge. The residue was then dissolved in methanol (5 ml) then treated with macroporous tosic acid (102 mg, 0.452 mmol) and stirred for 17 h at room temperature. Addition of 0.88 ammonia solution (0.5 ml) was followed by stirring at room temperature for a further 30 mins and then the mixture was separated using a hydrophobic frit. The organic layer was concentrated in vacuo and the residue purified by HPLC (Method E) to afford the title compound (8 mg).

Provenance & Evidence