Pyridine → HCID 10094756, compound

Temperature

0 °C

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3(R)-(tetrahydro-thiopyran-3-yl)-propionic acid (52 mg, 0.143 mmol) in methylene chloride (1 mL) was treated with N,N-dimethylformamide (0.1 mL) and then cooled to 0° C. The reaction mixture was treated with a 2.0M solution of oxalyl chloride in methylene chloride (143 μL, 0.286 mmol). The reaction mixture was stirred at 0° C. for 30 min, allowed to warm to 25° C., and then concentrated in vacuo to remove solvents and excess oxalyl chloride. The resulting residue was re-dissolved in dry tetrahydrofuran (1 mL) and was treated dropwise with a solution of 2-aminopyrazine (27.2 mg, 0.286 mmol) in tetrahydrofuran (1 mL) and pyridine (57.8 μL, 0.715 mmol). The resulting reaction mixture was stirred at 25° C. for 30 min. The reaction mixture was then diluted with water (2 mL) and extracted with methylene chloride (3×5 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 1/1 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-N-pyrazin-2-yl-3(R)-(tetrahydro-thiopyran-3-yl)-propionamide (44 mg, 69.8%) as a colorless gum: EI-HRMS m/e calcd for C19H22ClN3O3S2 (M+H)+ 440.0864, found 440.0867.

1. temperatureto warm to 25° C.
2. concentrationconcentrated in vacuo
3. customto remove solvents and excess oxalyl chloride
4. dissolutionThe resulting residue was re-dissolved in dry tetrahydrofuran (1 mL)
5. customThe resulting reaction mixture
6. stirringwas stirred at 25° C. for 30 min
7. extractionextracted with methylene chloride (3×5 mL)
8. dry with materialThe combined organic layers were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-322c6b9d2ff24ad0833f4d2296a19294

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105671B2