Ethylamine → HCID 24900850, compound

Participants

Reaction Conditions

Reaction Steps

To 3-(3-fluoro-4-nitro-phenylsulfanyl)-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine (50 mg, 0.135 mmol) was added a 2 M solution of ethylamine in THF (1 mL). The reaction mixture was stirred at 70° C. for 1 h, then it was concentrated in vacuo. The residue was suspended in formic acid (1 mL) and iron powder (75 mg, 1.35 mmol) was added. The reaction mixture was stirred at 100° C. for 16 h, then it was cooled to room temperature and the stir bar was removed with most of the iron. The mixture was concentrated in vacuo and the resulting residue was treated with 2 M aqueous sodium hydroxide. The precipitate was filtered, washed with water then diethyl ether. It was then diluted in 2 mL of DMSO, filtered through a 0.45 um filter, and the crude mixture was purified directly by mass-triggered HPLC (5-95% CH3CN/H2O, 0.1% HCOOH modifier) to provide 25 mg of 3-(3-ethyl-3H-benzoimidazol-5-ylsulfanyl)-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine as a white solid (49% yield).

Provenance & Evidence