Formic Acid → HCID 10341480, compound

Temperature

0 °C

A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydro-furan-2(R)-yl)-propionamide (0.060 g, 0.16 mmol) in formic acid (0.19 mL, 4.8 mmol) was cooled to 0° C. and then treated with a 30% aqueous hydrogen peroxide solution (0.10 mL, 0.8 mmol). The resulting solution was stirred at 0° C. for 30 min and was then quenched with a 10% aqueous sodium bisulfite solution. The reaction mixture was diluted with water (5 mL) and extracted with ethyl acetate (2×5 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was dissolved in methanol (1 mL) and was treated dropwise with a solution of potassium permanganate (0.028 g, 0.176 mmol) in water (0.5 mL). The dark brown solution was stirred at 25° C. for 30 min, and was then diluted with methanol (10 mL). The reaction mixture was filtered to remove solids, and the filtrate was concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 1/1 hexanes/ethyl acetate to 1/4 hexanes/ethyl acetate) afforded the 2-(3-chloro-4-methanesulfonyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydro-furan-2(R)-yl)-propionamide (44 mg, 67.1%) as a colorless gum: C18H20ClN3O4S (M+) 409.0863, found 409.0868.

1. customwas then quenched with a 10% aqueous sodium bisulfite solution
2. additionThe reaction mixture was diluted with water (5 mL)
3. extractionextracted with ethyl acetate (2×5 mL)
4. dry with materialThe combined organic layers were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. dissolutionThe resulting residue was dissolved in methanol (1 mL)
8. stirringThe dark brown solution was stirred at 25° C. for 30 min
9. filtrationThe reaction mixture was filtered
10. customto remove solids
11. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-805d7a6d81f146838a3a18b9dcdde04a

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105671B2