Diisopropylethylamine → HCID 44540867, compound

Participants

Reaction Conditions

Reaction Steps

To 3-(methylsulfonyl)-2-pyridinecarboxylic acid (which may be prepared as described by Blank, Benjamin; DiTullio, Nicholas W.; Owings, Franklin F.; Deviney, Linda; Miao, Clara K.; Saunders, Harry L. Journal of Medicinal Chemistry (1977), 20(4), 572-576.) (89 mg, 0.44 mmol) was added O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (172 mg, 0.45 mmol), DIPEA (0.106 ml) and DMF (1 ml). The reaction was stirred for 20 mins at 25° C. 6-(1H-Indol-4-yl)-1H-indazol-4-amine (50 mg, 0.20 mmol) was added and the reaction was stirred for a further 20 h at 25° C. The solvent was dried under a stream of nitrogen to give the crude product. This sample in DMF was loaded onto an aminopropyl cartridge (5 g) and after standing for 3 h, the column was washed with 10% methanol in dichloromethane. The appropriate fractions were combined and dried under a stream of nitrogen to give the crude product which was purified by Mass Directed Automated Preparative HPLC (Method B). The solvent was dried under a stream of nitrogen to give the title compound (29 mg).

Provenance & Evidence