Diisopropylethylamine → HCID 44540686, compound

Participants

Reaction Steps

A solution of 6-[(dimethylamino)methyl]-2-pyridinecarboxylic acid (27 mg, 0.15 mmol) in DMF (0.0008 ml) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (72 mg, 0.19 mmol) and DIPEA (0.052 ml). After 5 minutes the resulting solution was added to 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (33 mg, 0.10 mmol). After stirring for 90 mins at room temperature the mixture was treated with saturated sodium bicarbonate solution (10 ml) and extracted with dichloromethane (3×10 ml). The extracts were passed through a hydrophobic frit, combined and the solvent was evaporated under nitrogen flow. The residue was dissolved in methanol (2 ml) and hydrochloric acid (2M, 0.080 ml) was added. The solvents were evaporated under nitrogen stream to give a crude product which was purified by Mass Directed Automated Preparative HPLC (Method B). Fractions containing pure product were evaporated under a nitrogen stream to give the title compound (22 mg) as a pale solid.

Provenance & Evidence