Production Method 1

496-72-0

24424-99-5

885270-81-5

885270-77-9

Reaction Conditions

1.1 Reagents: Guanidine hydrochloride Solvents: Ethanol ;  2 h, rt

Reference

Discovery of a Selective Aurora A Kinase Inhibitor by Virtual Screening

Kilchmann, Falco; et al, Journal of Medicinal Chemistry, 2016, 59(15), 7188-7211

Production Method 2

496-72-0

24424-99-5

885270-81-5

885270-77-9

Reaction Conditions

1.1 Catalysts: Guanidine hydrochloride Solvents: Ethanol ;  5 min, 35 - 40 °C

Reference

Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups

Jahani, Fatemeh; et al, Tetrahedron Letters, 2011, 52(12), 1260-1264

Production Method 3

24424-99-5

885270-81-5

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  0 °C; overnight, rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  overnight, rt

Reference

2-Aminopyrimidine Derivatives as New Selective Fibroblast Growth Factor Receptor 4 (FGFR4) Inhibitors

Mo, Cheng; et al, ACS Medicinal Chemistry Letters, 2017, 8(5), 543-548

(2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester Raw materials

• 3,4-Diaminotoluene
• Di-tert-butyl dicarbonate

(2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester Preparation Products

• (2-Amino-5-methyl-phenyl)-carbamic Acid tert-butyl ester (885270-77-9)
• (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester (885270-81-5)

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• 4. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
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• 5. Estimation of activation energy for electroporation and pore growth rate in liquid crystalline and gel phases of lipid bilayers using molecular dynamics simulations?
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylcarbamic acid esters

Latest Research Insights on (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester (CAS: 885270-81-5)

In recent years, (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester (CAS: 885270-81-5) has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, known for its role as a key intermediate in the synthesis of various bioactive molecules, has been the subject of numerous studies aimed at exploring its potential applications in drug discovery and development. The unique structural features of this compound, including its tert-butyl carbamate group and amino-methyl substitution, make it a versatile building block for the construction of more complex pharmacophores.

Recent studies have focused on the synthetic utility of (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester in the preparation of kinase inhibitors and other targeted therapeutics. For instance, a 2023 publication in the Journal of Medicinal Chemistry highlighted its use in the synthesis of novel Bruton's tyrosine kinase (BTK) inhibitors, which are being investigated for the treatment of autoimmune diseases and certain cancers. The study demonstrated that the tert-butyl carbamate group serves as a protective moiety, enabling selective functionalization of the amino group under mild conditions.

Another area of active research involves the application of this compound in the development of positron emission tomography (PET) tracers. A recent study published in ACS Chemical Neuroscience reported the successful incorporation of (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester into a radiolabeled probe for imaging tau pathology in Alzheimer's disease. The researchers noted that the compound's stability and favorable pharmacokinetic properties make it an excellent candidate for further development as a diagnostic tool.

From a mechanistic perspective, computational studies have provided insights into the molecular interactions of derivatives of (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester with biological targets. Molecular docking simulations have revealed that these compounds can form stable hydrogen bonds with key residues in enzyme active sites, explaining their observed inhibitory activities. These findings have important implications for the rational design of next-generation therapeutics.

In terms of synthetic methodology, recent advances have focused on improving the efficiency and sustainability of the production processes for (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester. A 2024 Green Chemistry publication described a novel continuous flow synthesis approach that reduces solvent waste and improves yield compared to traditional batch methods. This development is particularly significant given the growing emphasis on green chemistry principles in pharmaceutical manufacturing.

Looking forward, the versatility of (2-Amino-4-methyl-phenyl)-carbamic acid tert-butyl ester suggests it will continue to play an important role in medicinal chemistry research. Ongoing studies are exploring its potential in the development of antiviral agents, particularly against emerging RNA viruses. Additionally, its application in the synthesis of proteolysis targeting chimeras (PROTACs) represents an exciting new direction in targeted protein degradation therapeutics.

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