Hydrazine → HCID 90373274, compound

To a solution of (E)-1,1-dimethyl-2-(1,1,1-trifluoropropan-2-ylidene)hydrazine (2.256 g, 14.63 mmol) in dry THF (20 mL) at −78° C. were added n,n,n′,n′-tetramethylethylenediamine (2.190 ml, 14.63 mmol) and lithium diisopropylamide, 2.0m heptane/tetrahydrofuran/ethylbenzene (7.32 ml, 14.63 mmol) and stirred at this temperature for 30 min. A solution of (R,E)-N-(2-fluoro-1-(2-fluoro-3-methylphenyl)ethylidene)-2-methylpropane-2-sulfinamide (2.0 g, 7.32 mmol) in toluene (12 mL) at −78° C. was treated with trimethylaluminum, 2.0m solution in toluene (3.66 ml, 7.32 mmol) for 10 min and added dropwise to the solution containing the hydrazine at −78° C. The resulting mixture was stirred at this temperature for 1.5 h. The mixture was quenched with saturated NH4Cl, and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-50% EtOAc/hexanes to afford a bright yellow oil as (R)-N-((Z)-4-(2,2-dimethylhydrazono)-1,5,5,5-tetrafluoro-2-(2-fluoro-3-methylphenyl)pentan-2-yl)-2-methylpropane-2-sulfinamide (5.66 g, 77% yield, combined). MS m/z=427.9 [M+H]+. Calculated for C18H26F5N3OS: 427.17.

1. additionadded dropwise to the solution
2. stirringThe resulting mixture was stirred at this temperature for 1.5 h
3. customThe mixture was quenched with saturated NH4Cl
4. extractionextracted with EtOAc
5. dry with materialThe combined organics were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customchromatographed on silica gel using 0-50% EtOAc/hexanes

ORD record

ord-5a57ae2416624dbb997c43a0eb7e0035

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296734B2