(6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;hydrochloride

Base Information

• Chemical Name: (6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;hydrochloride
• CAS No.: 104632-27-1
• Molecular Formula: C10H17N3S.2ClH
• Molecular Weight: 284.24896
• Hs Code.: 2934200000
• Mol file: 104632-27-1.mol

Synonyms:

Chemical Property of (6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;hydrochloride

Chemical Property:

• PSA: 79.91000
• LogP: 3.50720
• Storage Temp.: ?20°C
• Solubility.: H2O: >15mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 247.0909965
• Heavy Atom Count: 15
• Complexity: 188

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-PramipexoleDihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCNC1CCC2=C(C1)SC(=N2)N.Cl
• Isomeric SMILES: CCCN[C@@H]1CCC2=C(C1)SC(=N2)N.Cl
• Description: Pramipexole (Item No. 11981) is an agonist of dopamine receptors that has applications in Parkinson’s disease and other disorders. Pramipexole is usually available as a mixture of enantiomers, with the majority of the dopamine receptor-dependent activity resulting from the (S) form. (R)-Pramipexole is an enantiomer of pramipexole that is ~100-fold less active than the (S) form as a dopamine receptor agonist. For this reason, it can be used as a negative control for the (S) form in the study of dopamine receptors. Both isoforms are antioxidants that target mitochondria to prevent apoptosis. This cytoprotective effect of (R)-pramipexole, without dopaminergic side effects, suggests utility in amyotrophic lateral sclerosis.
• Uses: (R)-Pramipexole Dihydrochloride (Pramipexole EP Impurity D; Pramipexole BP Impurity D; Pramipexole USP Related Compound D) is the opposite enantiomer of Pramipexole (P700755), a dopamine-D2-receptor agonist. Dexpramipexole is a low-molecular-weight, water-soluble, orally bioavailable, renally excreted compound with linear pharmacokinetics. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements. Pramipexole may be used as a secondary pharma standard for the determination of the analyte in pharmaceutical formulations using reversed-phase high-performance liquid chromatography and ultraviolet spectrophotometry technique.

Technology Process of (6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;hydrochloride

There total 5 articles about (6R)-6-N-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R)-(+)-pramipexole (104632-28-2) → (R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride (104632-27-1,104617-85-8)

Guidance literature:

With hydrogenchloride; In Isopropyl acetate; at 15 ℃; for 1h; Product distribution / selectivity;

Reference yield: 92.0%

(R)-pramipexole p-tosylate → (R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride (104632-27-1,104617-85-8)

Guidance literature:

With hydrogenchloride; In tert-butyl methyl ether; water; at 0 - 5 ℃; Product distribution / selectivity;

Reference yield: 77.0%

(+)-2-amino-6-propionamidotetrahydrobenzothiazole (106006-85-3) → (R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride (104632-27-1,104617-85-8)

Guidance literature:

(+)-2-amino-6-propionamidotetrahydrobenzothiazole; With chloro-trimethyl-silane; In dichloromethane; at 0 - 15 ℃; Inert atmosphere;

With lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane; at -10 - 0 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.06.144

upstream raw materials:

(R)-(+)-pramipexole

(R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine

(+)-2-amino-6-propionamidotetrahydrobenzothiazole

propyl tosylate

Refernces

• 1、 Ravinder,Rajeswar Reddy,Panasa Reddy,Bandichhor, Rakeshwar. "Amide activation by TMSCl: Reduction of amides to amines by LiAlH 4 under mild conditions". supporting information. p. 4908 - 4913. Retrieved 2013/08/28.
• 2、 -. "COMPOSITIONS AND METHODS OF USING (R)-PRAMIPEXOLE". Page/Page column 99. . Retrieved 2010/04/03.