Hydrochloric Acid → N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

A mixture of N-[6-(3-nitrophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (3.84 g, 11.3 mmol), zinc (5.17 g, 79.1 mmol), hydroxylammonium chloride (3.02 g, 56.5 mmol) and methanol (30 mL) was stirred under refluxing conditions for 3 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (50 mL), and reduced iron (5.00 g, 89.5 mmol), concentrated hydrochloric acid (5 mL) and water (50 mL) were added. The mixture was stirred under refluxing conditions for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was collected by filtration and washed with ethyl acetate to give the title compound (862 mg, 25%) as a white solid.

1. filtrationThe reaction mixture was filtered through celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. dissolutionThe residue was dissolved in ethanol (50 mL)
4. stirringThe mixture was stirred under refluxing conditions for 1 hr
5. filtrationThe reaction mixture was filtered through celite
6. concentrationthe filtrate was concentrated under reduced pressure
7. filtrationThe residue was collected by filtration
8. washwashed with ethyl acetate

ORD record

ord-2138cd3a26b045c0848aa6ac23b8fb80

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304557B2