2,6-Benzothiazolediamine, 4,5,6,7-tetrahydro-N6-propyl-, hydrochloride (1:2), (6R)-

Dexpramipexole 2Hcl(KNS-760704), also known as R-(+)-Pramipexole, is a neuroprotective agent and weak non-ergoline dopamine agonist. IC50 Value:Target: Dopamine ReceptorDexpramipexole has been found to have neuroprotective effects and is being investigated for treatment of amyotrophic lateral sclerosis (ALS). Dexpramipexole reduces mitochondrial reactive oxygen species (ROS) production, inhibits the activation of apoptotic pathways, and increase cell survival in response to a variety of

General procedure: In typical experimental procedure for the Synthesis of (3aS, 12bS)-5-chloro-2-methyl-2, 3, 3a, 12b-tetrahydro-1H-dibenzo[2, 3:6, 7]oxepino[4, 5-c]pyrrolemaleate(1b’): Amide (1a) (10 g, 33.43 mmol) and DCM (100 mL) were charged into a round bottomed flask and stirred under nitrogen atmosphere for 10-15 minutes and cooled to 0-5°C. Trimethylsilyl chloride (5.1 mL, 40.12 mmol) was then added to the mixture over 10-15 minutes and stirred for 10-15 minutes at same temperature.Lithium aluminum hydride (19.5 mL, 46.81 mmol) in THF solution is added dropwise at -10-0°C. After complete addition, the solution is allowed to 0-10°C and stirring is continued for 1-2 hours. After completion of reaction (TLC), thereaction was quenched by slow dropwise addition of 2M sodium hydroxide (30 mL)and stirred for 10-15 minutes. Separate aqueous and organic layer. Extract the compound from aqueous layer with DCM (50.0 mL). Combine both the organic layerand wash with 20percent sodium chloride solution. Concentrate the DCM to get the crude which was dissolved in isopropyl alcohol (50.0 mL).The resulting solids were dried under high vacuum for 2 h and then taken up in 50 mL of ethanol and cooled to between 0 and 5° C. [002S7] - Conversion of (R)-pramipexole free base to (R)-pramipexole dihydrochloride:; The freebase of (R)-pramipexole (4.8 grams; 0.022 mol) was dissolved in 200 ml of IPAC and cooled to 15C. HCl gas was bubbled into the slurry for 1 hour. The mixture was then filtered, washed with IPAC and dried under vacuum at room temperature overnight. The final product was 6.4 grams of (R)-pramipexole dihydrochloride, indicative a of 100percent yield, and a 97percent chemical purity as determined by HPLC.