Ethylamine → HCID 24900850, compound

Temperature

70 °C

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).

1. concentrationit was concentrated in vacuo
2. stirringThe reaction mixture was stirred at 100° C. for 16 h
3. temperatureit was cooled to room temperature
4. customthe stir bar was removed with most of the iron
5. concentrationThe mixture was concentrated in vacuo
6. additionthe resulting residue was treated with 2 M aqueous sodium hydroxide
7. filtrationThe precipitate was filtered
8. washwashed with water
9. additionIt was then diluted in 2 mL of DMSO
10. filtrationfiltered through a 0.45 um
11. filtrationfilter
12. customthe crude mixture was purified directly by mass-triggered HPLC (5-95% CH3CN/H2O, 0.1% HCOOH modifier)

ORD record

ord-6523df5a19e146ba82e9263914e32fcb

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507489B2