Production Method 1

327030-39-7

937048-39-0

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C; 45 min, -78 °C
1.2 Reagents: Triisopropyl borate ;  -78 °C; 2 h, -78 °C; overnight, -78 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

CamkII inhibitors and uses thereof

, World Intellectual Property Organization, , ,

Production Method 2

937048-39-0

Reaction Conditions

Reference

Camkii inhibitors and uses thereof

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Production Method 3

327030-39-7

937048-39-0

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Toluene ,  Tetrahydrofuran ;  -70 °C; 30 min, -70 °C
1.2 Reagents: Triisopropyl borate ;  -70 °C; 70 °C → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt
1.4 Reagents: Phosphoric acid Solvents: Water ;  30 min, rt

Reference

Preparation of isoquinolines and related compounds as inhibitors of NHE-mediated antiport useful in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders

, World Intellectual Property Organization, , ,

Production Method 4

327030-39-7

937048-39-0

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Toluene ,  Tetrahydrofuran ,  Hexane ;  30 min, -78 °C; -78 °C → -20 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  -20 °C; -20 °C → rt

Reference

Alpha-substituted arylmethylpiperazine pyrazolo[1,5-a]pyrimidine amide derivatives as antiretroviral agents and their preparation and use in the treatment of HIV associated diseases

, World Intellectual Property Organization, , ,

Production Method 5

327030-39-7

937048-39-0

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  rt → -70 °C; 10 min, -70 °C; 1 h, -70 °C
1.2 Reagents: Triisopropyl borate ;  overnight, -70 °C → rt
1.3 Reagents: Sodium hydroxide ,  Water Solvents: Water ;  1 h, rt
1.4 Reagents: Phosphoric acid Solvents: Water ;  pH 6

Reference

Preparation of pyrrolo[2,1-f][1,2,4]triazin-4-ylamines as IGF-1R kinase inhibitors for the treatment of cancer and other hyperproliferative diseases

, World Intellectual Property Organization, , ,

(3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid Raw materials

• 1-boc-4-(3-bromophenyl)piperazine

(3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid Preparation Products

• (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid (937048-39-0)

• 1. Enabling chloride salts for thermal energy storage: implications of salt purity?
  J. Matthew Kurley,Phillip W. Halstenberg,Abbey McAlister,Stephen Raiman,Richard T. Mayes RSC Adv., 2019,9, 25602-25608
• 2. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002
• 3. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 4. Evidence of field induced slow magnetic relaxation in cis-[Co(hfac)2(H2O)2] exhibiting tri-axial anisotropy with a negative axial component?
  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
• 5. Fe(ii)-Assisted one-pot synthesis of ultra-small core–shell Au–Pt nanoparticles as superior catalysts towards the HER and ORR?
  Yi Cao,Yujiao Xiahou,Lixiang Xing,Xiang Zhang,Hong Li,ChenShou Wu,Haibing Xia Nanoscale, 2020,12, 20456-20466

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazinanes Phenylpiperazines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazinanes Piperazines Phenylpiperazines

Introduction to (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic Acid and Its Significance in Modern Chemical Biology

Compound with the CAS number 937048-39-0 is a specialized chemical entity that has garnered significant attention in the field of chemical biology and pharmaceutical research. The molecular structure of this compound, specifically (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid, presents a unique combination of functional groups that make it a valuable tool in the development of novel therapeutic agents. This introduction aims to provide a comprehensive overview of the compound's properties, applications, and its relevance to the latest advancements in the field.

The core structure of (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid consists of a phenyl ring substituted with a boronic acid moiety at the 3-position, further modified by a piperazine ring that is protected by a tert-butoxycarbonyl (Boc) group at the 4-position. This configuration imparts several advantageous characteristics to the compound, making it particularly useful in various biochemical and pharmacological applications.

Boronic acids are well-known for their ability to form reversible covalent bonds with hydroxyl groups, a property that has been leveraged in the development of protease inhibitors and other enzyme-targeting agents. The presence of the boronic acid group in (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid facilitates its interaction with biological targets, thereby enabling its use as a key intermediate in drug discovery and development.

The tert-butoxycarbonyl (Boc) group serves as an effective protecting group for the piperazine nitrogen, ensuring stability during synthetic procedures while maintaining the reactivity of the boronic acid moiety. This dual functionality makes the compound particularly versatile for use in multi-step synthetic routes, allowing for the efficient construction of complex molecular architectures.

In recent years, significant progress has been made in understanding the role of boronic acids in medicinal chemistry. For instance, research has demonstrated that boronic acid-containing compounds can exhibit potent inhibitory activity against various enzymes involved in disease pathways. This has led to the development of several clinical candidates that are currently undergoing evaluation for their therapeutic potential.

One notable area where (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid has shown promise is in the inhibition of carbonic anhydrase enzymes. Carbonic anhydrases are a family of enzymes that catalyze the reversible conversion of carbon dioxide and water to bicarbonate and protons, playing a crucial role in various physiological processes. Inhibitors of carbonic anhydrases have been investigated for their potential use in treating conditions such as glaucoma, altitude sickness, and certain types of cancer.

The piperazine moiety in (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid is particularly interesting from a structural perspective. Piperazine derivatives are known for their broad spectrum of biological activity, including antimicrobial, antifungal, and anti-inflammatory properties. By incorporating this group into a boronic acid-based framework, researchers can exploit its unique interactions with biological targets to develop novel therapeutic agents.

Recent studies have highlighted the importance of boronic acids in the development of targeted therapy strategies. For example, research has shown that boron-containing compounds can be selectively targeted to specific tissues or cells, making them attractive candidates for precision medicine approaches. The ability of (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid to form stable complexes with biological molecules opens up new possibilities for designing highly specific and effective therapeutic interventions.

The synthesis of (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid involves several key steps that highlight its complexity and versatility. The introduction of the boronic acid group typically requires careful control over reaction conditions to ensure high yield and purity. Additionally, the protection and deprotection steps associated with the Boc group must be carefully optimized to prevent unwanted side reactions.

In conclusion, compound CAS number 937048-39-0, specifically identified as (3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)phenyl)boronic acid, represents a significant advancement in chemical biology and pharmaceutical research. Its unique structural features and functional properties make it a valuable tool for developing novel therapeutic agents. As research continues to uncover new applications for boronic acids, compounds like this are likely to play an increasingly important role in addressing some of today's most pressing medical challenges.

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