Ammonia → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-3-isoxazolecarboxamide

Participants

Reaction Steps

5-Methyl-3-isoxazolecarboxylic acid (21 mg) was treated with anhydrous THF (2 ml) and then 1-chloro-N,N,2-trimethylpropenylamine (0.026 ml). The reaction was stirred at RT under nitrogen for 2 h. The reaction was then treated with anhydrous DIPEA (0.131 ml) and 2 ml of solution of 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (750 mg) in THF (30 ml). The reaction was then stirred at RT under nitrogen for 69 h. The solvent was blown off under a stream of nitrogen, dissolved in methanol (3 ml) and then the solvent removed under reduced pressure. The crude reaction mixture was dissolved in methanol (5 ml), treated with macroporous tosic acid resin (102 mg; 4.45 mmol/g) stirred at RT for 17 h and then treated with 0.88 ammonia (0.5 ml), stirred for 30 min and then filtered. The solvent was removed under reduced pressure and then purified by mass directed preparative HPLC (Method A) to give the title compound.

Provenance & Evidence