Lubeluzole

Base Information

• Chemical Name: Lubeluzole
• CAS No.: 144665-07-6
• Molecular Formula: C₂₂H₂₅F₂N₃O₂S
• Molecular Weight: 433.522
• European Community (EC) Number: 806-348-7
• UNII: V2SIB71583
• DSSTox Substance ID: DTXSID60162779
• Nikkaji Number: J615.844G
• Wikipedia: Lubeluzole
• Wikidata: Q6695177
• NCI Thesaurus Code: C170134
• ChEMBL ID: CHEMBL281724
• Mol file: 144665-07-6.mol

Synonyms:lubeluzole;R-91154

Chemical Property of Lubeluzole

Chemical Property:

• Vapor Pressure: 2.75E-14mmHg at 25°C
• Melting Point: 65.8°
• Boiling Point: 579.8°Cat760mmHg
• Flash Point: 304.5°C
• PSA: 77.07000
• Density: 1.327g/cm³
• LogP: 3.85290
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble2mg/mL, clear (warmed)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 433.16355455
• Heavy Atom Count: 30
• Complexity: 541

Purity/Quality:

97% ^*data from raw suppliers

Lubeluzole dihydrochloride ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C1CCN(CC1)CC(COC2=CC(=C(C=C2)F)F)O)C3=NC4=CC=CC=C4S3
• Isomeric SMILES: CN(C1CCN(CC1)C[C@@H](COC2=CC(=C(C=C2)F)F)O)C3=NC4=CC=CC=C4S3

Technology Process of Lubeluzole

There total 25 articles about Lubeluzole 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: 84.0%

2-chlorobenzo[d][1,3]thiazole (615-20-3) + 1-(3,4-difluorophenoxy)-3-(4-(methylamino)piperidin-1-yl)propan-2-ol (1425504-47-7) → lubeluzole (144665-07-6)

Guidance literature:

In water; at 120 ℃; for 0.5h; Solvent; Temperature; Time; Microwave irradiation;

DOI:10.1021/ol302601b

Reference yield: 83.0%

2-chlorobenzo[d][1,3]thiazole (615-20-3) + (S)-1-(3,4-difluorophenoxy)-3-(4-(methylamino)piperidin-1-yl)propan-2-ol (1425504-51-3) → lubeluzole (144665-07-6)

Guidance literature:

In water; at 120 ℃; for 0.5h; Microwave irradiation;

DOI:10.1021/ol302601b

Reference yield: 79.0%

(+)-(S)-3-(3,4-difluorophenoxy)-2-hydroxypropyl 4-methylbenzenesulfonate (1449846-90-5) + N-methyl-N-(piperidin-4-yl)-1,3-benzothiazol-2-amine (104605-42-7) → (-)-Lubeluzole (144665-07-6)

Guidance literature:

With potassium carbonate; In isopropyl alcohol; at 50 ℃; for 26h;

DOI:10.1016/j.bmcl.2013.06.077

upstream raw materials:

N-methyl-N-(piperidin-4-yl)-1,3-benzothiazol-2-amine

butan-1-ol

3,4-difluorophenol

2-chlorobenzo[d][1,3]thiazole

Refernces

• 1、 Kommi, Damodara N.,Kumar, Dinesh,Seth, Kapileswar,Chakraborti, Asit K.. "Protecting group-free concise synthesis of (RS)/(S)-lubeluzole". . p. 1158 - 1161. Retrieved 2013/04/24.
• 2、 -. "4-[(2-benzothiazolyl)methylamino]-alpha-[(3,4-difluorophenoxy)methyl]-1-piperidineethanol". . . Retrieved 2008/06/13.