106006-84-2

Basic information

• Product Name: (6S)-2-Amino-6-propionamidotetrahydrobenzothiazole
• Synonyms: (6S)-2-AMINO-6-PROPIONAMIDOTETRAHYDROBENZOTHIAZOLE;(S)-N-(2-AMINO-4,5,6,7-TETRAHYDRO-BENZOTHIAZOL-6-YL)-PROPIONAMIDE;(S)-2-AMINO-6-PROPIONAMIDO-4,5,6,7-TETRAHYDROBENZOTHIAZOLE;(-)-2-Amino-6-propionamido-tetrahydro-benzothiazole;(-)-2-amino-6-propionamido--4,5,6,7-tetrahydrobenzothiazole;(S)-2-AMINO-6-PROPIONAMIDOTETRAHYDROBENZOTHIAZOLE;s-2-amino-6-propionamide-4,5,6,7-tetrahydrobenzothiazole;N-[(6S)-2-amino-4,5,6,7-tetrahydro-6-benzothiazolyl]-Propanamide
• CAS NO: 106006-84-2
• Molecular Formula: C₁₀H₁₅N₃OS
• Molecular Weight: 225.31
• EINECS: 1806241-263-5
• Product Categories: intermidiate of Pramipexole;Chemical Amines;Amines;Chiral Reagents;Heterocycles;Pramipexole Dihydrochloride Monohydrate
• Mol File: 106006-84-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 187-1880C
• Boiling Point: 502.9 °C at 760 mmHg
• Flash Point: 257.9 °C
• Appearance: off-white solid
• Density: 1.26 g/cm³
• Vapor Pressure: 3.06E-10mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 15.52±0.20(Predicted)
• CAS DataBase Reference: (6S)-2-Amino-6-propionamidotetrahydrobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: (6S)-2-Amino-6-propionamidotetrahydrobenzothiazole(106006-84-2)
• EPA Substance Registry System: (6S)-2-Amino-6-propionamidotetrahydrobenzothiazole(106006-84-2)

Safety Data

• Hazardous Substances Data: 106006-84-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A pramipexole intermediate.

InChI:InChI=1/C10H15N3OS/c1-2-9(14)12-6-3-4-7-8(5-6)15-10(11)13-7/h6H,2-5H2,1H3,(H2,11,13)(H,12,14)/t6-/m0/s1

Upstream product

• 123-62-6 propionic acid anhydride 
• 106092-09-5 (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine 
• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 104617-50-7 N-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)acetamide hydrobromide 
• 375824-96-7 2-amino-6-(propionylamino)-4,5,6,7-tetrahydrobenzothiazole 
• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 

Downstream Products

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

Relevant articles and documents

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%.

A preparation method of pramipexole hydrochloride (by machine translation)

The invention discloses a method for preparation of pramipexole hydrochloride, comprises the following steps: 1) in the organic solvent, in order to 2, 6 - diamino - 4, 5, 6, 7 - tetrahydrobenzo and thiazole as the raw material, to join the resolving agent, heating to reflux, cooling, filtering, basified, make the (-) - (6 s) - 2, 6 - diamino 4, 5, 6, 7 - tetrahydrobenzo and thiazole; 2) in ethanol solution, the (-) - (6 s) - 2, 6 - diamino 4, 5, 6, 7 - tetrahydrobenzo and thiazole, and c anhydride reaction, by heating to reflux, to obtain (-) - (6 s) - 2 - amino - 6 - propionyl amino - 4, 5, 6, 7 - tetrahydrobenzo and thiazole; 3) (-) - (6 s) - 2 - amino - 6 - propionyl amino - 4, 5, 6, 7 - tetrahydrobenzo and thiazole in toluene solution in red aluminum reduction reaction, by heating to reflux, stirring, after devitrifying, make the use of pramipexole; the pramipexole into the isopropyl alcohol solution, by stirring, after devitrifying, react with hydrochloric acid, by decompression, drying, hydrochloride pramipexole. The preparation method is reaction low requirements on the equipment, the pramipexole prepared hydrochloric acid content is high, high purity, high solubility, the output is high, there is little impurity. (by machine translation)

A compound and its preparation method

The invention relates to a compound and a preparation method thereof, and specifically relates to an intermediate for synthesizing pramipexole dihydrochloride and a preparation method thereof. The intermediate is easy to purify. The synthesis of the intermediate comprises the following steps: subjecting (s)-2,6-diamino-4,5,6,7-tetrahydrobenzothiazole to carry out reactions with propionic anhydride, and then reducing the reaction products with a reductant so as to obtain the intermediate. The whole reaction process does not contain any intermediate treatment, and the preparation method has the advantages of simple reaction process, mild reaction conditions, high safety, high yield, and suitability for industrial production.