943319-02-6

Basic information

• Product Name: 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid
• Synonyms: 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid
• CAS NO: 943319-02-6
• Molecular Weight: 383.536
• Mol File: 943319-02-6.mol

Chemical Properties

• CAS DataBase Reference: 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid(943319-02-6)
• EPA Substance Registry System: 2-amino-6-propylamino-4,5,6,7-tetrahydrobenzothiazole p-toluenesulfonic acid(943319-02-6)

Safety Data

• Hazardous Substances Data: 943319-02-6(Hazardous Substances Data)

Usage

Structure

Consists of a benzothiazole ring with an amino group at the 2-position and a propylamino group at the 6-position, along with a p-toluenesulfonic acid group.

Application

Used as an intermediate in the synthesis of pharmaceuticals and agrochemicals.

Potential Uses

Treatment of neurological disorders.
Antifungal agent.

Solubility

The presence of p-toluenesulfonic acid group allows for easy solubility in polar solvents.

Versatility

Due to its solubility properties, it is versatile and useful in various chemical processes.

Upstream product

• 404892-23-5 2-Acetylamino-6-oxo-4,5,6,7-tetrahydrobenzothiazole 
• 159015-33-5 2-amino-6-(ethylenedioxy)-4,5,6,7-tetrahydrobenzothiazole 
• 144810-01-5 1,4-cyclohexanedione-1-ethylene acetal 4-trimethylsilyl enol ether 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 113030-24-3 2-amino-6-oxo-4,5,6,7-tetrahydrobenzothiazole 
• 599-91-7 propyl tosylate 
• 106092-09-5 (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine 

Downstream Products

• 104632-26-0 pramipexole 
• 104632-25-9 pramipexole dihydrochloride 
• 191217-81-9 pramipexole dihydrochloride monohydrate 

Relevant articles and documents

Baker's yeast catalyzed preparation of a new enantiomerically pure synthon of (S)-pramipexole and its enantiomer (dexpramipexole) This work is dedicated to Professor Enzo Santaniello in the year of his 70th birthday

A biocatalyzed reduction of a prochiral bicyclic ketone afforded enantiomerically pure (R)-2-acetylamino-6-hydroxy-4,5,6,7-tetrahydrobenzothiazole, a synthon of the anti-Parkinson (S)-pramipexole and its (R)-isomer, which is currently under investigation for the treatment of amyotrophic lateral sclerosis (ALS).

Industrial preparation method for pramipexole and hydrochloride thereof

The invention relates to a preparation method for S-(-)pramipexole. The method comprises the following steps: (1) dissolving S-(-)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole in a mixed solvent, carrying out stirring, adding a basic catalyst and n-propyl p-toluenesulfonate, carrying out heating after completion of addition, then carrying out a stirring reaction, and carrying out filtering and drying after completion of the reaction so as to obtain white S-(-)pramipexole p-toluenesulfonate solid; and (2) adding S-(-)pramipexole p-toluenesulfonate into an aqueous solution of salt, adding an inorganic base under stirring, carrying out stirring at room temperature after completion of addition, and carrying out filtering and drying so as to obtain a white S-(-)pramipexole solid, wherein no organic solvent is used in the step (2).

PROCESS FOR THE PREPARATION OF PRAMIPEXOLE BASE AND/OR ITS SALTS

The process for the preparation of pramipexole base and/or its pharmaceutically accepted salts, especially hydrochloride salt, is based on the reaction of (S)-(-)2,6-diamino-4,5,6,7-tetrahydrobenzothiazole with an alkylating agent, wherein the reaction is carried out with the absence of a base, in a solvent from which the resulting N-monoalkylated product selectively precipitates out as a salt, which, after isolation from the reaction mixture: a) upon the treatment of inorganic base is converted into free pramipexole base, and then into another pharmaceutically accepted pramipexole salt, or b) is converted directly into another pharmaceutically accepted pramipexole salt or the hydrate thereof.