Production Method 1

24424-99-5

7720-39-0

929568-19-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dichloromethane ,  Water ;  16 h, rt

Reference

Heteroaromatic compounds as TYK2 inhibitors and their preparation

, World Intellectual Property Organization, , ,

Production Method 2

24424-99-5

7720-39-0

929568-19-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dichloromethane ,  Water ;  14 h, rt

Reference

Design, synthesis, and evaluation of hinge-binder tethered 1,2,3-triazolylsalicylamide derivatives as Aurora kinase inhibitors

Jeong, Yunkyung; Lee, Jooyeon; Ryu, Jae-Sang, Bioorganic & Medicinal Chemistry, 2016, 24(9), 2114-2124

Production Method 3

24424-99-5

7720-39-0

929568-19-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dichloromethane ,  Water ;  16 h, rt

Reference

Preparation of novel 7-substituted derivatives of 3-carboxyoxadiazinoquinolones and their use as antibacterial agents

, World Intellectual Property Organization, , ,

Production Method 4

24424-99-5

7720-39-0

929568-19-4

Reaction Conditions

1.1 Solvents: Dichloromethane ,  Pyridine ;  10 min, rt; 10 min, 40 °C; 40 °C → 5 °C; 30 min, 5 °C; 24 h, rt

Reference

Preparation of pyrimidine derivatives as inhibitors of type I insulin-like growth factor receptor

, World Intellectual Property Organization, , ,

Production Method 5

929568-19-4

Reaction Conditions

Reference

Preparation of novel 7-substituted derivatives of 3-carboxyoxadiazinoquinolones and their use as antibacterial agents

, France, , ,

tert-butyl 2-aminoimidazole-1-carboxylate Raw materials

• Di-tert-butyl dicarbonate
• 2-Aminoimidazole

tert-butyl 2-aminoimidazole-1-carboxylate Preparation Products

• tert-butyl 2-aminoimidazole-1-carboxylate (929568-19-4)

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  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 4. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
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• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides
• Solvents and Organic Chemicals Organic Compounds

Tert-butyl 2-aminoimidazole-1-carboxylate (CAS No. 929568-19-4): A Comprehensive Overview

Tert-butyl 2-aminoimidazole-1-carboxylate (CAS No. 929568-19-4) is a versatile compound with significant applications in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique structural features, has garnered considerable attention due to its potential in the development of novel therapeutic agents. In this comprehensive overview, we will delve into the chemical properties, synthesis methods, biological activities, and recent advancements in the research and application of tert-butyl 2-aminoimidazole-1-carboxylate.

Chemical Properties and Structure

Tert-butyl 2-aminoimidazole-1-carboxylate is a derivative of imidazole, a five-membered heterocyclic compound with two nitrogen atoms. The presence of the tert-butyl group and the carboxylate moiety imparts unique chemical properties to this compound. The tert-butyl group, known for its steric bulk, provides enhanced stability and solubility characteristics. The carboxylate group, on the other hand, confers polarity and reactivity, making tert-butyl 2-aminoimidazole-1-carboxylate an attractive candidate for various chemical reactions.

The molecular formula of tert-butyl 2-aminoimidazole-1-carboxylate is C₈H₁₅N₃O₂, with a molecular weight of approximately 177.22 g/mol. The compound exists as a white crystalline solid at room temperature and is soluble in common organic solvents such as methanol, ethanol, and dimethyl sulfoxide (DMSO). These solubility properties make it suitable for use in various laboratory settings and pharmaceutical formulations.

Synthesis Methods

The synthesis of tert-butyl 2-aminoimidazole-1-carboxylate can be achieved through several well-established routes. One common method involves the reaction of tert-butyl carbamate with an appropriate imidazolium salt under basic conditions. This reaction typically proceeds via a nucleophilic substitution mechanism, leading to the formation of the desired product. Another approach involves the condensation of tert-butyl carbamate with an imidazole derivative in the presence of a coupling agent such as dicyclohexylcarbodiimide (DCC) or N,N'-diisopropylcarbodiimide (DIC).

Recent advancements in synthetic chemistry have also explored more efficient and environmentally friendly methods for the preparation of tert-butyl 2-aminoimidazole-1-carboxylate. For instance, microwave-assisted synthesis has been shown to significantly reduce reaction times and improve yields while minimizing byproduct formation. Additionally, the use of green solvents and catalysts has gained traction in efforts to develop sustainable synthetic protocols.

Biological Activities and Applications

Tert-butyl 2-aminoimidazole-1-carboxylate has been extensively studied for its biological activities and potential therapeutic applications. One of its key properties is its ability to act as a modulator of various biological pathways. Research has shown that this compound can inhibit specific enzymes involved in signal transduction processes, making it a valuable tool in drug discovery.

In particular, tert-butyl 2-aminoimidazole-1-carboxylate has demonstrated promising antiproliferative effects against cancer cells. Studies have reported that it can induce apoptosis in various cancer cell lines by disrupting cell cycle progression and inhibiting key oncogenic pathways. These findings have led to its evaluation as a potential anticancer agent in preclinical studies.

Beyond cancer research, tert-butyl 2-aminoimidazole-1-carboxylate has also shown potential in other therapeutic areas. For example, it has been investigated for its anti-inflammatory properties and its ability to modulate immune responses. Preclinical studies have indicated that this compound can reduce inflammation by inhibiting pro-inflammatory cytokine production and suppressing immune cell activation.

Clinical Trials and Future Prospects

The promising preclinical results with tert-butyl 2-aminoimidazole-1-carboxylate have paved the way for further clinical evaluation. Several clinical trials are currently underway to assess the safety and efficacy of this compound in various disease conditions. These trials aim to provide robust evidence supporting its potential as a therapeutic agent.

In addition to its direct therapeutic applications, tert-butyl 2-aminoimidazole-1-carboxylate serves as an important building block in the synthesis of more complex molecules with enhanced biological activities. Researchers are actively exploring strategies to modify this compound's structure to optimize its pharmacological properties and expand its therapeutic utility.

Tert-butyl 2-aminoimidazole-1-carboxylate's unique combination of chemical stability, solubility, and biological activity makes it an attractive candidate for further development in medicinal chemistry and pharmaceutical research. As ongoing studies continue to uncover new insights into its mechanisms of action and potential applications, this compound is poised to play a significant role in advancing our understanding of disease biology and developing novel therapeutic strategies.

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• 49761-82-2(N-Boc-Imidazole)
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• 82998-18-3(1H-Imidazole-1-carboxylic acid 1-methylethyl ester)
• 1186299-71-7(Tert-Butyl 2-((tert-butoxycarbonyl)amino)-1H-imidazole-1-carboxylate)
• 1935172-04-5(tert-butyl 2-(methylamino)imidazole-1-carboxylate)