Diisopropylethylamine → HCID 44540155, compound

Participants

Reaction Steps

A mixture 4-fluoro-1-methyl-1H-pyrazole-3-carboxylic acid and 4-fluoro-1-methyl-1H-pyrazole-5-carboxylic acid (45:55) (580 mg, 20% W/W), HATU (306 mg), and DIPEA (0.422 ml) in DMF (3 ml) was stirred at RT for 10 min. 6-(1H-Indol-4-yl)-1H-indazol-4-amine (100 mg) in DMF (3 ml) was then added and the mixture was stirred at RT overnight. The reaction mixture was added to a 20 g aminopropyl SPE cartridge which had been preconditioned with methanol. The reaction mixture was allowed to remain on the cartridge for 3 h before being eluted with methanol (4 column volumes) and then 10%-triethylamine in methanol (6 column volumes). The appropriate fractions were evaporated to give a brown oil which was partitioned between ethyl acetate (25 ml) and water (5 ml). The phases were separated and the organic phase was dried over anhydrous sodium sulphate and evaporated to a brown oil. This was dissolved in ethyl acetate (10 ml) and pre-adsorbed on silica (1.2 g) which was then added to the top of a 20 g silica SPE cartridge. The cartridge was eluted with a gradient of 0-100% ethyl acetate in cyclohexane over 60 min to give the title compound (65 mg) as a buff-coloured solid.

Provenance & Evidence