Diisopropylethylamine → N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Methyl-1,3-thiazole-4-carboxylic acid (4.59 g, 32.1 mmol), HATU (13.4 g, 35.3 mmol) and DIPEA (16.8 ml, 96 mmol) were stirred in DMF (140 ml) for 30 mins at 20° C. 6-Bromo-1H-indazol-4-amine (3.40 g, 16.03 mmol) was added and the reaction stirred at 20° C. for 2 days. The solvent was reduced to ˜40 ml and the reaction mixture applied to 5×70 g aminopropyl SPE cartridges and left to stand for 3 h. The cartridges were eluted with DCM:MeOH (1:1, v/v) and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography, eluting with 0-15% MeOH (containing 1% Et3N) in DCM. Appropriate fractions were evaporated to give the title compound 1.02 g.

Provenance & Evidence