Hydrochloric Acid → HCID 86611815, compound

To a solution of N-(2-tert-butoxycarbonyl)-ethylenediamine (0.63 ml, 4.00 mmol) and triethylamine (0.67 ml, 4.80 mmol) in dichloromethane (10 ml) was added 2-methoxyethanesulfonyl chloride (761 mg, 4.80 mmol) at 0° C., and the mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to obtain N-(2-tert-butoxycarbonylaminoethyl)-2-methoxyethanesulfonamide. The mixture of N-(2-tert-butoxycarbonylaminoethyl)-2-methoxyethanesulfonamide and 5N HCl (8 ml) in methanol (8 ml) was stirred at room temperature for 2 h, then at 50° C. for 1 h, and concentrated in vacuo to obtain N-(2-aminoethyl)-2-methoxyethanesulfonamide hydrochloride salt. The free base of the title compound was prepared following the method of Example 6 using methanesulfonic acid 3-[7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indol-3-yl]-([1,2,4]-thiadiazol-5-yl)methyl ester and N-(2-aminoethyl)-2-methoxyethanesulfonamide hydrochloride salt. The obtained crude free base of the title compound was purified by prep. LCMS to afford the trifluoroacetic acid salt of the title compound. EsIMS: m/z 528.0 [M+H]+.

1. waitat 50° C. for 1 h
2. concentrationconcentrated in vacuo

ORD record

ord-7eb158725df64762843857269368054f

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763732B2