104617-49-4

Basic information

• Product Name: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole
• Synonyms: 4,5,6,7-TETRAHYDRO-1,3-BENZOTHIAZOL-2,6-DIAMINE;4,5,6,7-tetrahydro-2,6-benzothiazole diamine;4,5,6,7-Tetrahydro-2,3-Benzothiazole Diamine;2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole;6-DiaMino-4;7-tetrahydrobenzothiazole;4,5,6,7-Tetrahydro-benzothiazole-2,6-diaMine;(RS)-N-Despropyl PraMipexole
• CAS NO: 104617-49-4
• Molecular Formula: C7H11N3S
• Molecular Weight: 169.25
• EINECS: 1308068-626-2
• Product Categories: Amines
• Mol File: 104617-49-4.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 359 °C at 760 mmHg
• Flash Point: 170.9 °C
• Appearance: off-white powder
• Density: 1.313 g/cm³
• Vapor Pressure: 2.45E-05mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Methanol (Slightly)
• PKA: 9.18±0.20(Predicted)
• CAS DataBase Reference: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(104617-49-4)
• EPA Substance Registry System: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(104617-49-4)

Safety Data

• Hazardous Substances Data: 104617-49-4(Hazardous Substances Data)

Usage

Uses

(RS)-N-Despropyl Pramipexole is an intermediate in the synthesis of Pramipexole (P700755), a dopamine-D2-receptor agonist; an antiparkinsonian agent.

InChI:InChI=1/C7H11N3S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h4H,1-3,8H2,(H2,9,10)

Upstream product

• 17356-08-0 thiourea 
• 687639-03-8 2-bromo-4-acetamidocyclohexanone 
• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 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 
• 106006-80-8 N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)acetamide 
• 104617-50-7 N-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)acetamide hydrobromide 
• 1315483-31-8 2,6-diamino-4,5,6,7-tetrahydro benzothiazole, (S)-tartarate salt 
• 873431-80-2 (S)-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine tartrate trihydrate 
• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 
• 202058-46-6 2-(3-bromo-4-oxocyclohexyl)isoindoline-1,3-dione 

Downstream Products

• 106092-11-9 (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine 
• 104632-28-2 (R)-(+)-pramipexole 

Relevant articles and documents

Dopamine autoreceptor agonists: Resolution and pharmacological activity of 2,6-diaminotetrahydrobenzothiazole and an aminothiazole analogue of apomorphine

The enantiomers of the aminothiazole analogues of the known dopaminergic agonists apomorphine (1) and 2-aminohydroxytetralin (2) have been prepared. The absolute configurations of the enantiomers of 2,6-diaminotetrahydrobenzothiazole have been established by X-ray crystallographic analysis. Dopamine (DA) autoreceptor agonist activities of the compounds were evaluated. Testing revealed (-)-5, the S enantiomer, to be the most active compound tested (inhibition of GBL accelerated dopamine synthesis and inhibition of α-methyltyrosine-induced decline of DA). In addition (-)-5 does not exhibit stereotyped behavior, suggesting a pronounced selectivity for DA autoreceptors.

Preparation method of high-purity pramipexole

The invention relates to the technical field of pharmacy, and provides a preparation method of high-purity pramipexole. According to the invention, raceme 2, 6-diamino 4, 5, 6, 7-tetrahydrobenzothiazole is used as an initial raw material, and pramipexole is obtained through a three-step chemical reaction, so the introduction of uncontrollable factors of drug quality is reduced, and the requirements of drug application are better met; the market price of the initial raw materials is low, so that the preparation cost of pramipexole can be greatly reduced; the solvent used in the method is green, environmentally friendly, cheap, easy to obtain and suitable for industrial production, the HPLC purity of the obtained pramipexole can reach 99.86%, and the isomer purity can reach 99.89%.

Crystallization process of diamino -4, 5, 6, 7- tetrahydrobenzothiazole

Reaction and formation, of the product, with acetone as a reaction solvent, takes place in acetone as a reaction solvent to give the product, as a raw material, with acetone as a reaction solvent to obtain the mixed rotation product, and then recrystallize the reaction solvent with water: to obtain the reaction . Example, shows that the reaction time, is greatly shortened by taking the product, as a reaction solvent by taking acetone as a reaction solvent as a raw material A; dropwise to obtain the reaction and the reaction of the reaction, solvent with water and dissolving: dropwise with acetone as a reaction solvent in step A as a reaction solvent in an existing production process by, acetone, L - taking acetone as a, reaction solvent to prepare a reaction solvent for, the whole process, to prepare a crystal, by taking acetone as, a reaction solvent to prepare a reaction solvent by taking acetone as a reaction solvent to prepare a. reaction solvent by taking acetone as a reaction solvent.

Industrial preparation method of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole

The invention discloses a preparation method of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole suitable for industrial production, wherein 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole is prepared by using p-acetamido cyclohexanone as a raw material through a one-pot method. According to the method, liquid bromine and acetic acid are not used in the production and preparation process, the 6-acetamido-2-amino-4,5,6,7-tetrahydro-benzothiazole can be prepared through a one-pot method, post-treatment operation is easy and convenient, the labor cost is saved, and the production cost is greatly reduced. The 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole prepared by the method is high in yield, good in purity and suitable for industrial production.