Hydrochloric Acid → HCID 71811244, compound

Temperature

0 °C

To a cooled solution (0° C.) of tert-butyl N-(4-methyl-2-pyridyl)-N-[2-[[(E)-3,3,3-trifluoroprop-1-enyl]sulfonyl-amino]ethyl]carbamate (190 mg, 0.464 mmol) in dioxane (10 ml) was added HCl (4M solution in dioxane, 3.5 ml, 14 mmol). The mixture was stirred at 0° C. for 30 minutes and then for 48 hours at room temperature. The mixture was evaporated to dryness under reduced pressure and the residue was partitioned between saturated sodium bicarbonate solution and DCM. Layers were separated and the aqueous layer was extracted with DCM (2×). The combined organic layers were dried over sodium sulfate, concentrated under reduces pressure and the residue was purified by column chromatography (silica, gradient of 10 to 100% heptane in ethyl acetate) to yield 103 mg of a white solid (0.33 mmol, 72%)

1. waitfor 48 hours at room temperature
2. customThe mixture was evaporated to dryness under reduced pressure
3. customthe residue was partitioned between saturated sodium bicarbonate solution and DCM
4. customLayers were separated
5. extractionthe aqueous layer was extracted with DCM (2×)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. concentrationconcentrated
8. customthe residue was purified by column chromatography (silica, gradient of 10 to 100% heptane in ethyl acetate)

ORD record

ord-d6641611dcfd44ed8e2f7743aefda8b4

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321724B2