Diisopropylethylamine → HCID 44540783, compound

Participants

Reaction Steps

A solution of 6-(4-morpholinylmethyl)-2-pyridinecarboxylic acid (33 mg, 0.15 mmol) in DMF (0.8 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). The mixture was stirred at room temperature for 15 mins then left to stand for 2 h. The reaction 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 (1 ml) and hydrochloric acid (2M, 0.080 ml) was added. After about 1 hour the solvent was evaporated under a stream of nitrogen 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 (11 mg) as a pale solid.

Provenance & Evidence