1H-Imidazol-2-carboxamide

Base Information

• Chemical Name: 1H-Imidazol-2-carboxamide
• CAS No.: 16093-82-6
• Molecular Formula: C4H5N3O
• Molecular Weight: 111.103
• Hs Code.: 2934999090
• Mol file: 16093-82-6.mol

Synonyms:Imidazole-2-carboxamide(8CI);2-Carbamoylimidazole;

Chemical Property of 1H-Imidazol-2-carboxamide

Chemical Property:

• Vapor Pressure: 1.58E-05mmHg at 25°C
• Melting Point: 312-313 °C (decomp)
• Refractive Index: 1.612
• Boiling Point: 365.4 °C at 760 mmHg
• PKA: 11.61±0.10(Predicted)
• Flash Point: 174.8 °C
• PSA: 71.77000
• Density: 1.394 g/cm³
• LogP: 0.20890
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

1H-Imidazole-2-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 1H-Imidazol-2-carboxamide (also known as Imidazole-2-carboxamide or 2-Carbamoylimidazole) is a chemical intermediate used in the synthesis of non-nucleoside adenosine deaminase (ADA) inhibitors. In the study, it served as a precursor or building block for designing potent and orally bioavailable ADA inhibitors, which were optimized for improved pharmacokinetics and therapeutic potential in anti-inflammatory and anti-leukemia applications. However, the abstract does not provide specific details about its direct role or properties beyond its inclusion as a reagent in the synthetic process.

Technology Process of 1H-Imidazol-2-carboxamide

There total 3 articles about 1H-Imidazol-2-carboxamide 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: 86.0%

5H,10H-diimidazo<1,2-a:1',2'-d>pyrazine-5,10-dione dihydrochloride (74840-92-9) → 1H-Imidazole-2-carbothioic acid amide (16093-82-6)

Guidance literature:

With ammonia; at 10 ℃; for 1h;

Reference yield: 36.0%

imidazole-2-carbonyl chloride → 1H-Imidazole-2-carbothioic acid amide (16093-82-6)

Guidance literature:

With ammonia; In water; at 10 ℃; for 1h;

Reference yield:

→ 1H-Imidazole-2-carbothioic acid amide (16093-82-6)

Guidance literature:

aus (6), H2, Ni;

DOI:10.1002/jhet.5570110431

upstream raw materials:

5H,10H-diimidazo<1,2-a:1',2'-d>pyrazine-5,10-dione dihydrochloride

Downstream raw materials:

2-cyano imidazole

Refernces

Structure-based design and synthesis of non-nucleoside, potent, and orally bioavailable adenosine deaminase inhibitors

10.1021/jm0499559

The study focuses on the structure-based design and synthesis of non-nucleoside adenosine deaminase (ADA) inhibitors, which are potent, orally bioavailable, and have potential as anti-inflammatory and anti-leukemia drugs. The researchers optimized a novel non-nucleoside ADA inhibitor, starting with compound 4 (Ki = 680 nM), and through structural optimization, they discovered compounds 5 (Ki = 11 nM), 6 (Ki = 13 nM), and 7 (Ki = 9.8 nM) with improved oral bioavailability (BA = 30-44%). These compounds were designed to target a hydrophobic cavity in the ADA enzyme and to resist metabolic clearance, leading to improved pharmacokinetics. The study also reports the in vivo efficacy of compound 6 in models of inflammation and lymphoma, marking it as the first orally effective ADA inhibitor. The chemicals used in the study include various aryl Grignard reagents, epoxides, imidazolecarboxamide, and other reagents for synthetic steps, as well as compounds 5-7 for biological evaluation. These chemicals served the purpose of creating and modifying the structure of ADA inhibitors to enhance their potency and bioavailability, ultimately aiming to develop more effective treatments for diseases related to ADA dysregulation.