Methanol → 3-Pyridinecarboxamide, 2-(((1,6-dihydro-6-oxo-3-pyridinyl)methyl)amino)-N-(3-(trifluoromethyl)phenyl)-

A mixture of 2-[(6-Methoxypyrid-3-yl)methylamino]-N-[3-(trifluoromethyl)phenyl]-3-pyridinecarboxamide (Example 4; 1.4 g, 3.65 mmol) and trimethylsilyl iodide (Fluka, Buchs, Switzerland; 1.4 mL, 10.3 mmol) in chloroform (30 mL) is stirred at 60° C. for 28 hours. The cooled mixture is then treated with methanol (2 mL) and stirred at room temperature for 10 minutes. The solvent is evaporated off under reduced pressure and the residue is treated with an aqueous solution of ammonia (100 mL of 10%) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with saturated aqueous sodium chloride (50 mL), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from hot ethyl acetate to give the title compound as a colourless crystalline solid, ma.p. 200-202° C.

1. stirringstirred at room temperature for 10 minutes
2. customThe solvent is evaporated off under reduced pressure
3. additionthe residue is treated with an aqueous solution of ammonia (100 mL of 10%)
4. extractionextracted with ethyl acetate (3×100 mL)
5. washThe combined extracts are washed with saturated aqueous sodium chloride (50 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. customthe solvent is evaporated off under reduced pressure
9. customto yield the crude product which
10. customis purified by recrystallisation from hot ethyl acetate

ORD-Eintrag

ord-976e31d53d654a46b8fe6d84a571da45

Quelldatensatz

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06624174B2