Lorediplon

Base Information

• Chemical Name: Lorediplon
• CAS No.: 917393-39-6
• Molecular Formula: C₂₀H₁₅FN₄O₂S
• Molecular Weight: 394.429
• UNII: VKU6Z23NSY
• ChEMBL ID: CHEMBL4303403
• DSSTox Substance ID: DTXSID00238684
• NCI Thesaurus Code: C170129
• Wikidata: Q6680290
• Wikipedia: Lorediplon
• Mol file: 917393-39-6.mol

Synonyms:lorediplon

Chemical Property of Lorediplon

Chemical Property:

• PSA: 95.81000
• LogP: 3.81060
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 394.08997507
• Heavy Atom Count: 28
• Complexity: 609

Purity/Quality:

99% ^*data from raw suppliers

Lorediplon >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N(C)C1=C(C=CC(=C1)C2=CC=NC3=C(C=NN23)C(=O)C4=CC=CS4)F
• Recent EU Clinical Trials: Double-blind, randomized, placebo-controlled cross-over dose finding study of two doses of lorediplon in adult patients with insomnia disorder
• Description: Lorediplon is a non-benzodiazepine belonging to pyrazolopyrimidine family isunderdevelopment for the management for insomnia. Lorediplon acts by modulationof the GABAgreceptor. Its long plasma half-life has the potential of hypnotic effect. Ithas the potential for maintenance of sleep and the sleep architecture. In the phase Ipharmacodynamic study,it showed better efficacy in quality and maintenance ofsleep as compared with zolpidem. It has been shown to be well tolerated, safe with noresidual effects as compared with other sedative-hypnotic. Currently, the drug has completed Phase ll clinical trial. Results indicated strongefficacy in sleep maintenance with an acceptable safety profile. It also seems topreserve natural sleep architecture.
• Uses: Lorediplon is GABAA receptor modulator and is used in the treatment of insomnia.

Technology Process of Lorediplon

There total 2 articles about Lorediplon 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: 86.5%

N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-methyl-acetamide (917393-46-5) + (5-amino-1H-pyrazol-4-yl)-thiophen-2-yl-methanone (96219-87-3) → Lorediplon (917393-39-6)

Guidance literature:

With acetic acid; at 75 ℃; for 4h;

Reference yield:

N-(5-acetyl-2-fluorophenyl)-N-acetamide (552301-41-4) → Lorediplon (917393-39-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / acetonitrile / 15 h / 15 - 30 °C

2: 8 h / Reflux

3: acetic acid / 4 h / 75 °C

With acetic acid; sodium hydroxide; In acetonitrile;

upstream raw materials:

N-[5-(3-dimethylamino-acryloyl)-2-fluoro-phenyl]-N-methyl-acetamide

(5-amino-1H-pyrazol-4-yl)-thiophen-2-yl-methanone

N-(5-acetyl-2-fluorophenyl)-N-acetamide

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF N-[5-(3-DIMETHYLAMINO-ACRYLOYL)-2-FLUORO-PHENYL]-N-METHYL-ACETAMIDE". Page/Page column 12. . Retrieved 2010/08/08.
• 2、 -. "Halogenated pyrazolo[1,5-a]pyrimidines, processes, uses, compositions and intermediates". Page/Page column 13. . Retrieved 2008/06/13.