Dimethyl Sulfoxide → HCID 67121130, compound

Temperature

-78 °C

A solution of oxalyl chloride (30 μL, 0.34 mmol) in dichloromethane (1 mL) was cooled to −78° C. A solution of dimethylsulfoxide (48 μL, 0.675 mmol) in dichloromethane (0.5 mL) was added drop wise and the mixture was stirred for 5 minutes at −78° C. A solution of 4-chloro-5-(4-fluorophenyl)-N-(3-hydroxycyclohexyl)isoxazole-3-carboxamide (104 mg, 0.307 mmol) in tetrahydrofuran (3 mL) and (0.5 mL) dichloromethane was added over 5 minutes and the reaction mixture was to stirred for 15 minutes at −78° C. Triethylamine (0.215 mL, 1.53 mmol) was added and the reaction was stirred for 10 minutes at −78° C., then allowed to warm to room temperature and stir for an additional 20 minutes. Water was added and the mixture was extracted three times with dichloromethane. The combined organic extracts were dried over MgSO4, filtered, concentrated in vacuo, and purified by silica gel chromatography, eluting with 2% methanol in dichloromethane to give the title compound (19.7 mg, 0.058 mmol). MS (ESI) m/z (M+H+): 337.2/339.2

1. stirringto stirred for 15 minutes at −78° C
2. stirringthe reaction was stirred for 10 minutes at −78° C.
3. temperatureto warm to room temperature
4. stirringstir for an additional 20 minutes
5. extractionthe mixture was extracted three times with dichloromethane
6. dry with materialThe combined organic extracts were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. custompurified by silica gel chromatography
10. washeluting with 2% methanol in dichloromethane

ORD record

ord-11c84090be18484bb925bc6682add1ce

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211927B2