460747-73-3

Basic information

• Product Name: (2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE
• Synonyms: (2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE;1-(3-BUTYNYL)-2(R)-METHYLPYRROLIDINE;Pyrrolidine, 1-(3-butynyl)-2-methyl-, (2R)- (9CI);(R)-1-(but-3-yn-1-yl)-2-methylpyrrolidine
• CAS NO: 460747-73-3
• Molecular Formula: C₉H₁₅N
• Molecular Weight: 137.2221
• Product Categories: AMINETERTIARY
• Mol File: 460747-73-3.mol

Chemical Properties

• Boiling Point: 185.4±23.0 °C(Predicted)
• Appearance: /
• Density: 0.890±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9?+-.0.40(Predicted)
• CAS DataBase Reference: (2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE(460747-73-3)
• EPA Substance Registry System: (2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE(460747-73-3)

Safety Data

• Hazardous Substances Data: 460747-73-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structural features and potential reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
(2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE is used as an intermediate in the development of new pharmaceutical compounds. Its unique structure and potential reactivity may contribute to the discovery of novel drug candidates with improved therapeutic properties.
Used in Materials Science:
(2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE is used as a component in the development of new materials with specific properties. Its unique structural features may contribute to the creation of advanced materials for various applications, such as sensors, catalysts, or functional coatings.
Further research and analysis are required to fully understand the potential uses and effects of (2R)-1-BUT-3-YN-1-YL-2-METHYLPYRROLIDINE in various applications.

Upstream product

• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 584-08-7 potassium carbonate 
• 765-38-8 (R)-(-)-2-methylpyrrolidine 
• 41720-98-3 (R)-2-methylpyrrolidine hydrochloride 

Downstream Products

• 1610838-96-4 (R)-2-methyl-1-(2-(5-(4-nitrophenoxy)benzofuran-2-yl)ethyl)pyrrolidine 
• 1610838-95-3 (R)-2-methyl-1-(2-(5-(4-fluorophenoxy)benzofuran-2-yl)ethyl)pyrrolidine 
• 1610838-94-2 (R)-2-methyl-1-(2-(5-(2-nitrophenoxy)benzofuran-2-yl)ethyl)pyrrolidine 
• 1610838-90-8 (R)-(3-iodophenyl)(2-(2-(2-methylpyrrolidin-1-yl)ethyl)benzofuran-5-yl)methanone 
• 1610838-89-5 (R)-(2-(2-(2-methylpyrrolidin-1-yl)ethyl)benzofuran-5-yl)(2-nitrophenyl)methanone 
• 1359168-20-9 (R)-(2-(2-(2-methylpyrrolidin-1-yl)ethyl)benzofuran-5-yl)(4-nitrophenyl)methanone 
• 804518-42-1 4-bromo-2-[4-(2-(R)-methyl-pyrrolidin-1-yl)-but-1-ynyl]-phenylamine 
• 460748-56-5 N-methoxy-N-methyl-3-(2-(2-[2(R)-methyl-1-pyrrolidinyl]ethyl)-1-benzofuran-5-yl)benzamide 
• 460748-55-4 3-(2-(2-[2(R)-methyl-1-pyrrolidinyl]ethyl)-1-benzofuran-5-yl)benzoic acid 
• 460748-44-1 1-[3-(2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)phenyl]ethanone 

Relevant articles and documents

Synthesis and biological evaluation of XB-1 analogues as novel histamine H3 receptor antagonists and neuroprotective agents

A novel class of H3 receptor antagonists, XB-1 analogues based on benzophenone or oxydibenzene scaffolds were synthesized, and their biological activities were evaluated to determine their in vitro neuroprotective effects against Aβ25-35-induced damage in primary cortical neurons and against glutamate-induced neuronal injury in primary cerebellar granule neurons. The results indicated that all of the tested analogues displayed neuroprotective activity at 0.1 μM or 1 μM. These findings may provide new insights into the development of novel promising H3 receptor antagonists with potential neuroprotective activity.

An efficient and convergent synthesis of the potent and selective H3 antagonist ABT-239

An efficient and convergent process for the preparation of a potent and selective H3 receptor antagonist, ABT-239, 1A was accomplished with an overall yield of 64%. The key step in the synthesis is a Sonogashira coupling/cyclization reaction of 1-but-3-ynyl-2-(R)-methylpyrrolidine (9) with 4′-hydroxy-3′-iodo-biphenyl-4-carbonitrile (3). Additionally, the key amine component 2-(R)-methylpyrrolidine (7) was effectively synthesized from the readily available Boc-l-prolinol with a simple catalytical hydrogenolysis as the key step. This column chromatography-free process is highlighted by several simple work-up and purification procedures and is amendable to the large-scale preparation of 1A.

Synthesis and SAR of 5-amino- and 5-(aminomethyl)benzofuran histamine H3 receptor antagonists with improved potency

A new series of H3 receptor antagonists was discovered with nanomolar and subnanomolar affinities at human and rat H3 receptors. Starting from an earlier, more structurally limited series of benzofurans, the present series of compounds demonstrated increased structural variety and flexibility with greater in vitro potency. One compound in particular, {2-[2-(2-(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}(5-nitropyridin-2-yl) amine (7h), gave the best binding potency (human Ki of 0.05 nM, rat Ki of 0.11 nM), which represented a 9-fold (in human) and an 11-fold (in rat) improvement over ABT-239 (compound 5), a compound previously reported to have excellent in vitro potency and in vivo efficacy. The synthesis, SAR of the H3 binding affinities, in vitro assay for phospholipidosis, and pharmacokinetic properties of the new compounds are described.

Structure-activity relationships of arylbenzofuran H3 receptor antagonists

An SAR study of histamine H3 receptor antagonists based on substituted (R)-2-methyl-1-[2-(5-phenyl-benzofuran-2-yl)-ethyl]-pyrrolidines is presented.

4-(2-[2-(2(R)-Methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention

H3 receptor antagonists based on a 2-aminoethylbenzofuran skeleton have been discovered, which are potent in vitro at human and rat H 3 receptors, with Ki values of 0.1-5.8 nM. Analogues were discovered with potent (0.01-1 mg/kg) cognition and attention enhancing properties in animal models. One compound in particular, 4-(2-[2-(2(R)- methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile (ABT-239), combined potent and selective H3 receptor antagonism and excellent pharmacokinetic and metabolic properties across species, with full efficacy in two behavioral models: a five-trial inhibitory avoidance acquisition model in rat pups at 0.1 mg/kg and a social recognition memory model in adult rats at 0.01 mg/kg. Furthermore, this compound did not stimulate locomotor activity and showed high selectivity for the induction of behavioral efficacy versus central nervous system based side effects. The potency and selectivity of this compound and of analogues from this class support the potential of H3 receptor antagonists for the treatment of cognitive dysfunction.

Fused bicyclic-substituted amines as histamine-3 receptor ligands

Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands and methods for using such compounds and compositions.

PROCESS FOR PREPARING AMINE-SUBSTITUTED BENZOFURANS

The present invention relates to processes for preparing amine substituted benzofurans, and more particularly 4-(2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile, and salts thereof. Compounds prepared by the processes of the invention have demonstrated activity as histamine-3 receptor ligands.

Fused bicyclic-substituted amines as histamine-3 receptor ligands

Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions comprising the histamine-3 receptor ligands and methods for using such compounds and compositions.