Diisopropylethylamine → 6-Bromo-N'-(4-morpholinylacetyl)-1H-indazole-4-carbohydrazide

Participants

Reaction Conditions

Reaction Steps

O-(7-Azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (0.841 g, 2.212 mmol) was dissolved in N,N-dimethylformamide (5 ml) then treated with 4-morpholinylacetic acid (0.304 g, 2.092 mmol) and then N,N-diisopropyethylamine (0.386 ml, 2.212 mmol). The clear solution was stirred at 20° C. for 10 mins then to this was added 6-bromo-1H-indazole-4-carbohydrazide (0.513 g, 2.011 mmol) as a partial solution in N,N-dimethylformamide (8 ml). The clear solution was stirred at 20° C. for 72 h under nitrogen. It was then reduced in volume to ˜1 ml, diluted with methanol (5 ml) and loaded onto an aminopropyl cartridge which had been pre-conditioned with methanol. The fully-loaded cartridge was left to stand for 2 h then eluted with methanol and the eluant evaporated to give an orange oil. This was diluted with dichloromethane (3 ml) and loaded onto a silica (10 g) cartridge. This was eluted with a gradient of methanol and ethyl acetate to give the title compound as a beige solid (0.792 g).

Provenance & Evidence