1083326-26-4

Basic information

• Product Name: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide
• Synonyms: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide;5-Sulfamoylpyridine-3-boronic acid pinacol ester;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-Pyridinesulfonamide
• CAS NO: 1083326-26-4
• Molecular Formula: C₁₁H₁₇BN₂O₄S
• Molecular Weight: 284
• Mol File: 1083326-26-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide(1083326-26-4)
• EPA Substance Registry System: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide(1083326-26-4)

Safety Data

• Hazardous Substances Data: 1083326-26-4(Hazardous Substances Data)

Usage

Description

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide is a pyridine derivative chemical compound with the molecular formula C13H19BN2O4S. It features a boron atom and a sulfonamide group, making it a versatile reagent in organic synthesis and a valuable building block in medicinal chemistry.

Uses

Used in Organic Synthesis:
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide is used as a reagent for cross-coupling reactions, facilitating the formation of carbon-carbon and carbon-heteroatom bonds. Its unique molecular structure and properties make it a valuable tool in this application, enhancing the efficiency and selectivity of synthetic processes.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide is used as a building block for the synthesis of various pharmaceutical compounds. Its incorporation into drug molecules can contribute to the development of new therapeutic agents with improved pharmacological properties.
Used in Chemical Research:
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide is also utilized in chemical research as a valuable tool for exploring new reaction mechanisms, developing novel synthetic methodologies, and understanding the fundamental principles of chemical reactivity. Its unique structure and properties provide researchers with new avenues for investigation and discovery in the field of chemistry.

Upstream product

• 16133-25-8 Pyridine-3-sulfonyl chloride 
• 65001-21-0 5-bromopyridine-3-sulphonyl chloride 
• 636-73-7 3-pyridinesulfonic acid 
• 62009-33-0 5-bromopyridine-3-sulfonamide 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1092565-14-4 5-{8-[3-(aminosulfonyl)phenyl]-1,5-naphthyridin-2-yl}-3-pyridinesulfonamide 
• 1272353-82-8 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 
• 1092565-19-9 5-[8-(3-cyanophenyl)-1,5-naphthyridin-2-yl]-3-pyridinesulfonamide 

Relevant articles and documents

Selective IKur Inhibitors for the Potential Treatment of Atrial Fibrillation: Optimization of the Phenyl Quinazoline Series Leading to Clinical Candidate 5-[5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide

We have recently disclosed 5-phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine 1 as a potent IKur current blocker with selectivity versus hERG, Na and Ca channels, and an acceptable preclinical PK profile. Upon further characterization in vivo, compound 1 demonstrated an unacceptable level of brain penetration. In an effort to reduce the level of brain penetration while maintaining the overall profile, SAR was developed at the C2′ position for a series of close analogues by employing hydrogen bond donors. As a result, 5-[5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide (25) was identified as the lead compound in this series. Compound 25 showed robust effects in rabbit and canine pharmacodynamic models and an acceptable cross-species pharmacokinetic profile and was advanced as the clinical candidate. Further optimization of 25 to mitigate pH-dependent absorption resulted in identification of the corresponding phosphoramide prodrug (29) with an improved solubility and pharmacokinetic profile.

QUINAZOLINES AS POTASSIUM ION CHANNEL INHIBITORS

A compound of formula (I) wherein A, X, Y, Z, R1 and R24 are described herein. The compounds are useful as inhibitors of potassium channel function and in the treatment and prevention of arrhythmia, IKur-associated disorders, and other disorders mediated by ion channel function.