Ammonium Chloride → HCID 67181910, compound

Temperature

-78 °C

(R,E)-N-((5-chloro-1-methyl-1H-pyrazol-4-yl)methylene)-2-methylpropane-2-sulfinamide (100 mg, 0.404 mmol) was dissolved in dichloromethane (10 ml) placed under nitrogen and cooled to −78° C. 1.4M methyl magnesium bromide solution (toluene:THF 3:1, 1.04 ml, 1.45 mmol) was added dropwise and reaction stirred overnight while warming to room temperature. Saturated aqueous ammonium chloride solution (20 ml) was added to the reaction and stirred for 5 minutes. The product was extracted with EtOAc (2×15 ml), combined organics were washed with brine (15 ml), dried over Na2SO4, filtered and concentrated and purified by silica gel column chromatography eluted with heptane/ethyl acetate=100/0 to 0/100 to furnish the title product as a clear gum (57 mg, 53% yield). 1H NMR (400 MHz, CD3OD) 1.18-1.19 (9H s) 1.54-1.56 (3H d) 3.81-3.82 (3H s) 4.41-4.47 (1H q) 7.50-7.51 (1H s) MS (ESI) m/z 264 (M+H)+

1. customreaction
2. temperaturewhile warming to room temperature
3. stirringstirred for 5 minutes
4. extractionThe product was extracted with EtOAc (2×15 ml)
5. washcombined organics were washed with brine (15 ml)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified by silica gel column chromatography
10. washeluted with heptane/ethyl acetate=100/0 to 0/100

ORD record

ord-51589c0e9360402086496564f04a268e

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964732B2