Ammonium Chloride → N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

To a solution of N-[6-(3-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (622 mg, 1.84 mmol) in methanol (10 mL) was added palladium carbon (50% water-containing product, 50 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (20 mL), and ammonium chloride (300 mg, 5.61 mmol) and zinc (360 mg, 5.51 mmol) were added. The mixture was stirred under refluxing conditions for 2 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (NH silica gel, ethyl acetate) to give the title compound (275 mg, 49%) 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 methanol (20 mL)
4. stirringThe mixture was stirred under refluxing conditions for 2 hr
5. filtrationThe reaction mixture was filtered through celite
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by column chromatography (NH silica gel, ethyl acetate)

ORD-Eintrag

ord-f6853152d4af46a5baed801ee4febc82

Quelldatensatz

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08304557B2