Oxalyl chloride → 2-cyclopentyl-N-[2-[2-[[3-(trifluoromethyl)-phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide

254 μl (3.0 mmol) oxalylchloride were added to a solution of 192 mg (1.5 mmol) 2-cyclopentyl acetic acid in DCM (10 ml) and the mixture was stirred for 3 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with dioxane (6 ml). This solution was added at 0° C. to a solution of 362 mg (1.0 mmol) [2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine (VPF-001) in dioxane (5 ml). Then the reaction solution was mixed with 420 mg (5.0 mmol) NaHCO3 and stirred for 16 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with water. Then it was extracted with EE and the organic phase was washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 3:1) of the residue yielded 231 mg (0.5 mmol, 54%) 2-cyclopentyl-N-[2-[2-[[3-(trifluoromethyl)-phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide. MS: m/z 473.1 [M+H]+.

1. concentrationThen the mixture was concentrated to small volume under vacuum
2. stirringstirred for 16 h at RT
3. concentrationThen the mixture was concentrated to small volume under vacuum
4. extractionThen it was extracted with EE
5. washthe organic phase was washed with a saturated aqueous NaHCO3 solution and brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated to small volume under vacuum

ORD record

ord-f3d7acdb66b34357b84229ab5fdef5cc

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247573B2