2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (CAS 1211443-61-6): A Comprehensive Overview
2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (CAS 1211443-61-6) is a highly significant chemical compound in the field of organic chemistry. This compound has attracted considerable attention due to its unique chemical structure and potential applications in various industries. In this article, we will delve into the details of this compound, including its basic information, physical and chemical properties, uses, applications in different fields, and the methods of its preparation.
Basic Information
The chemical name of this compound is 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide. Its CAS number is 1211443-61-6, which serves as a unique identifier in the chemical industry. The molecular formula of 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide is C14H17ClN4O, and its molecular weight can be calculated based on the atomic weights of its constituent elements. This compound is part of the pyrrolopyrimidine family, which is known for its diverse biological activities.
Physical and Chemical Properties
2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide exhibits certain physical and chemical properties that are crucial for understanding its behavior and potential applications. In terms of its physical state, it is typically a solid at room temperature. The melting point and boiling point of this compound are important parameters that determine its stability and handling conditions. However, specific values for these properties may vary depending on the purity and preparation method of the compound.
Chemically, this compound contains a chloro group (-Cl), a cyclopentyl group, and a dimethyl amide group attached to the pyrrolopyrimidine core. The presence of these functional groups imparts specific reactivity to the compound. For example, the chloro group can undergo substitution reactions under appropriate conditions, which can be exploited for the synthesis of derivatives with potentially enhanced biological activities. The cyclopentyl group provides hydrophobicity to the molecule, which may affect its solubility and interaction with biological membranes.
The solubility of 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide in different solvents is another important property. It is generally sparingly soluble in water but may show better solubility in organic solvents such as dimethyl sulfoxide (DMSO), ethanol, and acetonitrile. This solubility behavior is important for its use in biological assays and chemical synthesis, as it determines the appropriate solvents for dissolution and formulation.
Uses
2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide has a wide range of uses, primarily in the pharmaceutical and chemical research fields. In the pharmaceutical industry, it serves as a key intermediate for the synthesis of various drugs. Its unique chemical structure makes it a valuable building block for the development of new therapeutic agents targeting specific biological pathways.
One of the main applications of this compound is in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and dysregulation of kinase activity is associated with various diseases, including cancer. 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide can be used as a starting material to design and synthesize kinase inhibitors that can selectively target specific kinases, thereby blocking abnormal cell signaling and inhibiting tumor growth.
In addition to its use in drug development, this compound also has applications in chemical research. It can be used as a model compound for studying the reactivity and properties of pyrrolopyrimidine derivatives. By modifying its structure and studying the resulting changes in reactivity and biological activity, researchers can gain a better understanding of the structure-activity relationships of this class of compounds, which can guide the design of more effective drugs and chemical agents.
Applications in Different Fields
Pharmaceutical Industry
As mentioned earlier, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide is widely used in the pharmaceutical industry for drug discovery and development. In cancer research, it has shown potential as a lead compound for the development of novel anticancer drugs. By inhibiting specific kinases involved in tumor growth and metastasis, drugs derived from this compound can potentially provide more effective treatment options for cancer patients.
In addition to cancer, this compound may also have applications in the treatment of other diseases, such as autoimmune disorders. Kinases are also involved in the regulation of the immune system, and dysregulation of kinase activity can lead to autoimmune diseases. By targeting specific kinases with inhibitors based on 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide, it may be possible to develop new therapies for autoimmune disorders.
Chemical Research
In chemical research, this compound is used as a starting material for the synthesis of various pyrrolopyrimidine derivatives. By introducing different functional groups at specific positions on the pyrrolopyrimidine core, researchers can create a library of compounds with diverse structures and properties. These derivatives can then be screened for their biological activities, such as antibacterial, antifungal, and antiviral activities. This approach, known as combinatorial chemistry, allows for the rapid discovery of new chemical entities with potential therapeutic applications.
Biotechnology
In the biotechnology field, 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide can be used in the development of biosensors and diagnostic tools. By conjugating this compound with specific biomolecules, such as antibodies or nucleic acids, it can be used to detect and quantify specific biomarkers in biological samples. This can be useful for early disease diagnosis and monitoring of treatment response.
Preparation Methods
The preparation of 2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide typically involves a multi-step synthesis process. One common approach starts with the synthesis of the pyrrolopyrimidine core structure, followed by the introduction of the chloro, cyclopentyl, and dimethyl amide groups.
Step 1: Synthesis of the Pyrrolopyrimidine Core
The pyrrolopyrimidine core can be synthesized through a series of condensation and cyclization reactions. For example, a suitable pyrrole derivative can be reacted with a pyrimidine derivative in the presence of a base and a catalyst to form the pyrrolopyrimidine ring system. The reaction conditions, such as temperature, reaction time, and choice of solvents, need to be carefully optimized to ensure high yields and purity of the product.
Step 2: Introduction of the Chloro Group
Once the pyrrolopyrimidine core is synthesized, the chloro group can be introduced at the appropriate position. This can be achieved by reacting the pyrrolopyrimidine with a chlorinating agent, such as thionyl chloride or phosphorus oxychloride. The reaction conditions need to be carefully controlled to avoid over-chlorination and the formation of unwanted side products.
Step 3: Introduction of the Cyclopentyl Group
The cyclopentyl group can be introduced through a substitution reaction. A suitable cyclopentyl reagent, such as cyclopentyl bromide or cyclopentyl magnesium bromide, can be reacted with the chloro-substituted pyrrolopyrimidine in the presence of a base and a catalyst. The reaction conditions need to be optimized to ensure high yields and regioselectivity.
Step 4: Introduction of the Dimethyl Amide Group
Finally, the dimethyl amide group can be introduced by reacting the cyclopentyl-substituted pyrrolopyrimidine with dimethylamine in the presence of a coupling agent, such as N,N’-dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). The reaction conditions need to be carefully controlled to ensure high yields and purity of the final product.
References
- Reference 1: General Information on Pyrrolopyrimidine Derivatives
- Reference 2: Kinase Inhibitors and Their Applications
- Reference 3: Chemical Synthesis of Pyrrolopyrimidine Compounds