Oxalyl chloride → N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide

To a solution of 6-methylpyridine-2-carboxylic acid (5.66 g, 41.3 mmol) in tetrahydrofuran (300 mL) were added N,N-dimethylformamide (5 drops) and oxalyl chloride (7.20 mL, 83.0 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylacetamide (200 mL). A solution of 5-(3-aminophenoxy)pyridin-2-amine (7.90 g, 39.3 mmol) in N,N-dimethylacetamide (20 mL) was added with stirring at room temperature, and the mixture was stirred at room temperature for 65 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate-hexane to give the title compound (10.4 g, 83%) as a pale-brown solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in N,N-dimethylacetamide (200 mL)
3. stirringwith stirring at room temperature
4. stirringthe mixture was stirred at room temperature for 65 hr
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with water and saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltrated
9. concentrationThe filtrate was concentrated under reduced pressure
10. washthe residue was washed with ethyl acetate-hexane

ORD-Eintrag

ord-67706247f21840f089b392de08d9bc9e

Quelldatensatz

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08304557B2