Potassium Carbonate → N-pyrimidinyl piperidine sulfonamide

Temperature

85 °C

Part G: Preparation of methyl 1-(2-pyrimidinyl)4-[[4-[4-(trifiuoromethyl)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate. To a slurry of the piperidine sulfonamide from part F (6.3 g, 12.0 mmol) in methanol (25 mL) was added ammonium formate (2.2 g, 34.5 mmol). The system was purged with nitrogen for 10 min. The nitrogen stream was removed and palladium on carbon (1.2 g of 10 weight % on activated carbon, 50% water) was added. The reaction was refluxed for forty five min, cooled, filtered through Celite under N2, and concentrated in vacuo. The residue (6.21 g, 13.8 mmol) was dissolved in dry dimethylformamide (28 mL) and potassium carbonate (5.7 g, 41.4 mmol) and 2-chloropyrimidine (3.16 g, 27.6 mmol) were added. The reaction was stirred at 85° C. for one hr and then concentrated in vacuo. The residue was taken up in ethyl acetate and filtered through Celite. The filtrate washed with water two times, saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. The product was recrystallized (methanol) to give the N-pyrimidinyl piperidine sulfonamide as a white solid (4.94 g, 68%).

1. customThe system was purged with nitrogen for 10 min
2. customThe nitrogen stream was removed
3. additionpalladium on carbon (1.2 g of 10 weight % on activated carbon, 50% water) was added
4. temperatureThe reaction was refluxed for forty five min
5. temperaturecooled
6. filtrationfiltered through Celite under N2
7. concentrationconcentrated in vacuo
8. concentrationconcentrated in vacuo
9. filtrationfiltered through Celite
10. washThe filtrate washed with water two times, saturated sodium chloride solution
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe product was recrystallized (methanol)

ORD record

ord-51745ffb7986420291eb7196d0d464fe

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06372758B1