2-Methyl-2-propanyl [(3-cyano-1H-pyrazol-5-yl)methyl]methylcarbamate
[CAS# 1454849-40-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 2-Methyl-2-propanyl [(3-cyano-1H-pyrazol-5-yl)methyl]methylcarbamate
• Synonyms: tert-butyl N-[(3-cyano-1H-pyrazol-5-yl)methyl]-N-methylcarbamate
• Molecular Formula: C₁₁H₁₆N₄O₂
• Molecular Weight: 236.27
• CAS Registry Number: 1454849-40-1
• SMILES: CC(C)(C)OC(=O)N(C)CC1=CC(=NN1)C#N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 416.4±33.0 ºC 760 mmHg (Calc.)^*
• Flash point: 205.6±25.4 ºC (Calc.)^*
• Index of refraction: 1.532 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

2-Methyl-2-propanyl [(3-cyano-1H-pyrazol-5-yl)methyl]methylcarbamate is a carbamate derivative featuring a pyrazole ring substituted with a cyano group at the 3-position and a methylene-linked carbamate at the 5-position. The tert-butyl (2-methyl-2-propanyl) group on the carbamate confers steric protection, enhancing stability and controlling reactivity of the carbamate functional group.

The compound can be synthesized by reacting 3-cyano-5-(bromomethyl)pyrazole or a similar activated pyrazole derivative with a tertiary alcohol-derived carbamoyl chloride under basic conditions. This approach allows selective formation of the carbamate linkage while preserving the integrity of the pyrazole ring. Reaction conditions such as solvent, temperature, and base choice are critical to achieving high yields and minimizing side reactions like hydrolysis or over-alkylation.

2-Methyl-2-propanyl [(3-cyano-1H-pyrazol-5-yl)methyl]methylcarbamate is primarily used as a building block in medicinal chemistry. The pyrazole ring is a common pharmacophore in drug design, offering hydrogen-bonding capabilities and aromatic character for binding to biological targets. The cyano group provides electronic modulation and serves as a synthetic handle for further derivatization, while the carbamate moiety contributes to bioavailability and metabolic stability in potential pharmaceutical candidates.

The tert-butyl carbamate group can be selectively deprotected under acidic conditions to expose a free amine, allowing stepwise synthesis of more complex molecules. This feature is especially useful in combinatorial chemistry and peptide conjugation strategies, where controlled release of reactive sites is necessary. The molecule’s structure also enables participation in nucleophilic substitution, cross-coupling, or cyclization reactions to generate diverse derivatives for structure-activity relationship studies.

Physically, the compound is typically obtained as a crystalline solid or viscous oil, depending on the purification method. It exhibits moderate solubility in polar aprotic solvents such as dimethylformamide, tetrahydrofuran, and dichloromethane. Storage under anhydrous and inert conditions is recommended to prevent hydrolysis of the carbamate group or decomposition of the cyano-substituted pyrazole.

Overall, 2-Methyl-2-propanyl [(3-cyano-1H-pyrazol-5-yl)methyl]methylcarbamate is a versatile intermediate in synthetic and medicinal chemistry. Its combination of a pyrazole core, cyano functionalization, and sterically protected carbamate provides both chemical stability and synthetic flexibility, making it suitable for the construction of biologically active compounds, agrochemicals, and advanced heterocyclic derivatives.

References

2013. Macrocyclic derivatives for the treatment of proliferative diseases. WO Patent.
URL: WO-2013132376-A1

2013. Macrocyclic derivatives for the treatment of diseases. US Patent.
URL: US-8680111-B2

2015. Macrocyclic derivatives for the treatment of diseases. US Patent.
URL: US-9133215-B2