Methyl iodide → HCID 90029415, compound

Temperature

0 °C

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(2-hydroxyethyl)-N,N,4-trimethyl-1H-pyrazole-1-sulfonamide (compound 305.2, 636 mg, 2.73 mmol) in THF (10 mL). Sodium hydride (131 mg, 60% in mineral oil, 3.27 mmol) was added at 0° C. and stirred for 30 min at 0° C. This was followed by the addition of CH3I (204 μL, 3.28 mmol). The reaction mixture was stirred for 3 h at room temperature. The reaction was quenched with 10 mL of NH4Cl (sat.) and the aqueous phase was extracted with 3×50 mL of EtOAc. The combined organic phases were dried over Na2SO4. After filtration, the filtrate was concentrated under reduced pressure to give the crude product which was purified by silica gel chromatography with hexanes/EtOAc (15:1-8:1) as the eluent to give 452 mg (67%) of the title compound as a yellow oil.

1. customInto a 50-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe reaction mixture was stirred for 3 h at room temperature
4. customThe reaction was quenched with 10 mL of NH4Cl (sat.)
5. extractionthe aqueous phase was extracted with 3×50 mL of EtOAc
6. dry with materialThe combined organic phases were dried over Na2SO4
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. customto give the crude product which
10. customwas purified by silica gel chromatography with hexanes/EtOAc (15:1-8:1) as the eluent

ORD record

ord-5bf3a1f5de0d4173a3a13ab5f27bbefa

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2