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) is added a 2 M solution of ethylmagnesium chloride (0.19 mL, 0.38 mmol) in diethyl ether. After 2.5 hours, the reaction mixture is quenched with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (2×10 mL). The combined organic layers are washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane to afford an oil. The oil is dissolved in methanol (5 mL) and a 4 N solution of HCl in dioxane (0.5 mL, 2 mmol) is added. After 1 hour, the solution is concentrated to obtain the title compound.

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

ORD record

ord-70b54f4d5e3f4906a871bc68970875ab

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927550B2