Hydrochloric Acid → 1-Ethyl-1-(2-methanesulfonyl-thiazol-5-yl)-propylamine hydrochloride

To a chilled (0° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (100 mg, 0.3 mmol) in THF (5 mL) was added a 2 M solution of ethylmagnesium chloride (0.19 mL, 0.38 mmol) in diethyl ether. After 2.5 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane to yield an oil. The oil was dissolved in methanol (5 mL) and a 4 N solution of HCl in dioxane (0.5 mL, 2 mmol) was added. After 1 hour, the solution was concentrated to obtain the title compound.

1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL)
2. extractionextracted with EtOAc (2×10 mL)
3. washThe combined organic layers were washed with brine (10 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by silica gel chromatography
8. washeluting with a gradient of 0-10% methanol in dichloromethane
9. customto yield an oil
10. waitAfter 1 hour
11. concentrationthe solution was concentrated

ORD record

ord-73e474d4ab43457eb6da9d26de354676

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063065B2