Tasimelteon

Base Information

• Chemical Name: Tasimelteon
• CAS No.: 609799-22-6
• Deprecated CAS: 209255-28-7
• Molecular Formula: C15H19NO2
• Molecular Weight: 245.321
• European Community (EC) Number: 612-059-5
• UNII: SHS4PU80D9
• DSSTox Substance ID: DTXSID70209826
• Nikkaji Number: J3.640.465E
• Wikipedia: Tasimelteon
• Wikidata: Q7687250
• NCI Thesaurus Code: C152515
• RXCUI: 1490468
• Pharos Ligand ID: YCFN6NCZU12S
• Metabolomics Workbench ID: 152126
• ChEMBL ID: CHEMBL2103822
• Mol file: 609799-22-6.mol

Synonyms:BMS 214778;BMS-214778;BMS214778;N-((2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)propanamide;tasimelteon

Chemical Property of Tasimelteon

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 78 °C
• Refractive Index: 1.564
• Boiling Point: 442.553 ºC at 760 mmHg
• PKA: 16.43±0.46(Predicted)
• Flash Point: 221.448 ºC
• PSA: 38.33000
• Density: 1.146 g/cm³
• LogP: 2.64210
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 245.141578849
• Heavy Atom Count: 18
• Complexity: 318

Purity/Quality:

99% ^*data from raw suppliers

Tasimelteon-D5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Sedatives and Hypnotics
• Canonical SMILES: CCC(=O)NCC1CC1C2=C3CCOC3=CC=C2
• Isomeric SMILES: CCC(=O)NC[C@@H]1C[C@H]1C2=C3CCOC3=CC=C2
• Recent ClinicalTrials: The Effects of Tasimelteon in Participants With REM Behavior Disorder (RBD)
• Recent EU Clinical Trials: A multicenter, double-blind, randomized study to evaluate the effects of tasimelteon vs. placebo in participants with Delayed Sleep-Wake Phase Disorder (DSWPD)
• Description: Tasimelteon, which is marketed by Vanda Pharmaceuticals as Hetlioz and developed in partnership with Bristol-Myers Squibb, is a drug that was approved by the US FDA in January 2014 for the treatment of non-24-hour sleep–wake disorder (also called Non-24, N24 and N24HSWD). Tasimelteon is a melatonin MT1 and MT2 receptor agonist; because it exhibits a greater affinity to the MT2 receptor than MT1, is also known as Dual Melatonin Receptor Agonist.234 Two randomized controlled trials (phases II and III) demonstrated that tasimelteon improved sleep latency and maintenance of sleep with a shift in circadian rhythms, and therefore has the potential to treat patients with transient insomnia associated with circadian rhythm sleep disorders. Preclinical studies showed that the drug has similar phase-shifting properties to melatonin, but with less vasoconstrictive effects.
• Uses: Tasimelteon is a novel drug, used in the treatment of non-24 hour sleep-wake disorder. It helps to correct the circadian rhythm disorder often seen in patients who are visually impaired.

Technology Process of Tasimelteon

There total 39 articles about Tasimelteon 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: 97.7%

1-[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methanamine (209257-15-8,1400898-49-8) + propionyl chloride (79-03-8) → [14C]-Tasimelteon (609799-22-6)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 2h; Concentration; Solvent; Inert atmosphere;

Reference yield: 95.0%

1-[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methanamine (1S)-(+)-10-camphorsulfonic acid salt + propionic acid anhydride (123-62-6) → [14C]-Tasimelteon (609799-22-6)

Guidance literature:

1-[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methanamine (1S)-(+)-10-camphorsulfonic acid salt; With sodium hydroxide; In water; toluene; at 20 - 25 ℃; for 1.5h;

propionic acid anhydride; In water; toluene; at 0 - 10 ℃; for 0.5h; Temperature; Concentration;

Reference yield: 79.9%

C20H27NO4 → [14C]-Tasimelteon (609799-22-6)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 20 ℃; for 2h;

upstream raw materials:

4-ethenyl-2,3-dihydro-1-benzofuran

1-[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methanamine

propionyl chloride

2-(2,6-dichlorophenyl)ethan-1-ol

Refernces

• 1、 -. "Preparation method of tasimelteon". . . Retrieved 2020/07/21.
• 2、 Li, Xi-An,Yue, Lirong,Zhu, Jianrong,Ren, Huazhong,Zhang, Hong,Hu, Dong-yan,Han, Guangtian,Feng,Nan, Ze-dong. "Total synthesis of Tasimelteon". supporting information. p. 1986 - 1988. Retrieved 2019/07/03.