Dexpramipexole

Base Information

• Chemical Name: Dexpramipexole
• CAS No.: 104632-28-2
• Molecular Formula: C10H17 N3 S
• Molecular Weight: 211.331
• Hs Code.: 2934999090
• UNII: WI638GUS96
• DSSTox Substance ID: DTXSID50146624
• Nikkaji Number: J2.994.449K
• Wikipedia: Dexpramipexole
• Wikidata: Q5268345
• NCI Thesaurus Code: C169899
• Pharos Ligand ID: BZUF4BCZV8PH
• Metabolomics Workbench ID: 155297
• ChEMBL ID: CHEMBL249420
• Mol file: 104632-28-2.mol

Synonyms:2 Amino 6 propylaminotetrahydrobenzothiazole;2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole;2-amino-6-propylaminotetrahydrobenzothiazole;4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine;6,7-tetrahydro-N6-propyl-2,6-benzothiazolediamine dihydrochloride monohydrate;dexpramipexole;KNS 760704;KNS-760704;KNS760704;Mirapex;pramipexol;pramipexol dihydrobromide, (+-)-isomer;pramipexol dihydrochloride, (S)-isomer;pramipexol, (+-)-isomer;pramipexol, (R)-isomer;pramipexole;Pramipexole Dihydrochloride;Pramipexole Dihydrochloride Anhydrous;Pramipexole Hydrochloride Monohydrate;Sifrol;SND 919;SND 919CL2x;SND-919;SND-919CL2x;SND919CL2x

Chemical Property of Dexpramipexole

Chemical Property:

• Melting Point: 270-272°C
• Boiling Point: 378.0±42.0 °C(Predicted)
• PKA: 9.47±0.20(Predicted)
• PSA: 83.52000
• Density: 1.17±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 4.38490
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Sparingly, Sonicated), Water (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 211.11431873
• Heavy Atom Count: 14
• Complexity: 188

Purity/Quality:

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

Pramipexole Related Compound D United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCNC1CCC2=C(C1)SC(=N2)N
• Isomeric SMILES: CCCN[C@@H]1CCC2=C(C1)SC(=N2)N
• Recent ClinicalTrials: A Study to Assess the Effect of Dexpramipexole in Adolescents and Adults With Eosinophilic Asthma
• Recent EU Clinical Trials: A randomized, double-blind, placebo-controlled, parallel group study to assess the efficacy, safety, and tolerability of dexpramipexole administered orally for 52 weeks in participants with severe eosinophilic asthma
• Uses: (R)-Pramipexole enantiomer. A dopamine-D2-receptor agonist. Antiparkinsonian The opposite enantiomer of Pramipexole (P700755), harmacokinetics.

Technology Process of Dexpramipexole

There total 9 articles about Dexpramipexole 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: 85.5%

(R)-pramipexole p-tosylate → (R)-(+)-pramipexole (104632-28-2)

Guidance literature:

With sodium hydroxide; In water; at 10 ℃; for 0.25h; pH=~ 11 - ~ 12; Product distribution / selectivity;

Reference yield: 74.0%

2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole (104617-86-9) → (R)-(+)-pramipexole (104632-28-2) + pramipexole (104632-26-0)

Guidance literature:

2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole; Purification / work up; Resolution of racemate;

Reference yield:

D-tartaric acid (147-71-7,138508-61-9) + 2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole (104617-86-9) → (R)-(+)-pramipexole (104632-28-2) + pramipexole (104632-26-0)

Guidance literature:

D-tartaric acid; 2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole; In water; at 20 - 75 ℃; for 16h; Industry scale; Resolution of racemate;

With hydrogenchloride; In water; at 0 - 5 ℃;

With sodium hydroxide; In water; pH=~ 9 - ~ 10; Purification / work up;

upstream raw materials:

(+)-2-amino-6-propionamidotetrahydrobenzothiazole

2,6-diamino-4,5,6,7-tetrahydro-benzthiazole

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

2-amino-4,5,6,7-tetrahydro-6-propylaminobenzothiazole

Downstream raw materials:

(+)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethanone

(+)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-phenylpiperazin-1-yl)ethanone

(+)-2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propylamino)-1-(4-(2-methoxyphenyl)piperazin-1-yl)ethanone

(R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride

Refernces

• 1、 -. "COMPOSITIONS AND METHODS OF USING (R)-PRAMIPEXOLE". Page/Page column 98-99. . Retrieved 2010/04/03.
• 2、 -. "NOVEL PROCESS". Page/Page column 9-11. . Retrieved 2008/06/13.