Ammonia → HCID 44540785, compound

Participants

Reaction Steps

A mixture of 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (50 mg, 0.15 mmol), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (63 mg, 0.17 mmol) and 3-pyridinecarboxylic acid (20 mg, 0.16 mmol) was treated with DMF (2 ml) and DIPEA (0.052 ml). The reaction was stirred at room temperature for approximately 67.5 hours, then the solvent was removed in vacuo and the residue dissolved in methanol (3 ml). This was treated with macroporous p-toluenesulfonic acid resin (loading 1.43 mmol/g, 316 mg, 0.45 mmol), stirred for approximately 2 hours and then overnight, then treated with ammonia solution (0.88, 0.30 ml). The mixture was stirred for 5 mins, then the resin was filtered and the filtrate evaporated (blown down). The residue was purified by Mass Directed Automated Preparative HPLC (Method B). One fraction was evaporated to give the title compound (22 mg) as a yellow solid.

Provenance & Evidence