Indiplon

Base Information

• Chemical Name: Indiplon
• CAS No.: 325715-02-4
• Molecular Formula: C20H16N4O2S
• Molecular Weight: 376.439
• European Community (EC) Number: 608-755-3
• UNII: 8BT63DA42E
• DSSTox Substance ID: DTXSID80186270
• Nikkaji Number: J1.855.248E
• Wikipedia: Indiplon
• Wikidata: Q6024927
• NCI Thesaurus Code: C74385
• Metabolomics Workbench ID: 153552
• ChEMBL ID: CHEMBL262075
• Mol file: 325715-02-4.mol

Synonyms:indiplon;NBI 34060

Chemical Property of Indiplon

Chemical Property:

• Refractive Index: 1.699
• PKA: -1.42±0.50(Predicted)
• PSA: 95.81000
• Density: 1.35 g/cm³
• LogP: 3.67150
• Storage Temp.: Store at +4°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 376.09939694
• Heavy Atom Count: 27
• Complexity: 574

Purity/Quality:

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

Indiplon ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N(C)C1=CC=CC(=C1)C2=CC=NC3=C(C=NN23)C(=O)C4=CC=CS4
• Recent ClinicalTrials: An Exploratory Study of NBI-34060 Capsules and Next Day Functioning
• Description: Indiplon is a pyrazolopyrimidine that acts as a high-affinity positive allosteric modulator of the GABAA receptor, potentiating GABA-activated chloride currents in a dose-dependent and reversible manner. Indiplon is selective for α1 subunits (EC50 = 2.6 nM) as compared with α2, α3, or α5 (EC50 = 24, 60, and 77 nM). Through this action, indiplon has sedative and hypnotic effects that can improve sleep onset, maintenance, and duration.
• Uses: Indiplon is a member of pyrimidines with sedative, hypnotic. Indiplon has been used in trials studying the treatment of Insomnia and Depression.
• Clinical Use: Indiplon is a novel sedative-hypnotic recently approved for the treatment of insomnia. Like other non-benzodiazepine hypnotics, its mechanism of action is to modulate subunits, especially the alpha-1 subunit, of the GABA receptor complex in order to induce sedation. Indiplon was developed in two different formulations to address two different types of insomnia complaint: indiplon-IR (immediate release) was designed for sleep onset difficulties, while indiplon-MR (modified release) was developed for sleep maintenance insomnia.

Technology Process of Indiplon

There total 9 articles about Indiplon 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: 90.0%

(3-amino-1H-pyrazol-4-yl)(thien-2-yl)methanone (96219-87-3) + N-[(3-dimethylaminoacryloyl)phenyl]-N-methylacetamide → N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-a]-pyrimidin-7-yl}phenyl)acetamide (325715-02-4)

Guidance literature:

In acetic acid; for 3h; Heating / reflux;

Reference yield: 58.0%

2-Acetylthiophene (88-15-3,97511-16-5) + N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide (96605-65-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-a]-pyrimidin-7-yl}phenyl)acetamide (325715-02-4)

Guidance literature:

2-Acetylthiophene; N,N-dimethyl-formamide dimethyl acetal; With tris(N,N-dimethylbutyl)benzylammonium chloride; at 150 ℃; for 1h;

With hydroxylamine; at 150 ℃; for 5h;

N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide; Reagent/catalyst; Temperature; Further stages;

Reference yield:

(3-amino-1H-pyrazol-4-yl)(thien-2-yl)methanone (96219-87-3) + N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide (96605-65-1) → N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-a]-pyrimidin-7-yl}phenyl)acetamide (325715-02-4)

Guidance literature:

In dichloromethane; acetic acid;

upstream raw materials:

(3-amino-1H-pyrazol-4-yl)(thien-2-yl)methanone

N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide

N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-a]pyrimidin-7-yl}phenyl)acetamide hydrate

maleic acid

Downstream raw materials:

N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-a]pyrimidin-7-yl}phenyl)acetamide hydrate

Refernces

• 1、 -. "Processes for the Preparation of Indiplon and Intermediates Thereof". . . Retrieved 2012/02/06.
• 2、 -. "Method of using substituted pyrazolo [1,5-a] pyrimidines". Page/Page column 47. . Retrieved 2010/10/20.