Methyl 2-aminothiazole-5-carboxylate

China [CN]

Basic Information

Chemical Structure: The parent structure of this compound is a thiazole ring (a five-membered heterocyclic ring containing sulfur and nitrogen). An amino group (-NH₂) is attached at position 2 of the thiazole ring, and a methyl carboxylate group (-COOCH₃) is attached at position 5. It is a nitrogen- and sulfur-containing heterocyclic carboxylic acid ester derivative.

Main Uses: It is an important pharmaceutical intermediate, widely used in the synthesis of various drugs, such as:

Some antibacterial drugs: Based on the structural characteristics of the thiazole ring, it can participate in constructing molecular skeletons with antibacterial activity.

Certain anti-inflammatory and antiviral drugs: The amino and ester groups on the heterocyclic ring are key sites for active group modification, allowing for the introduction of different substituents through chemical reactions to optimize drug activity.

It can also be used in the development of lead compounds for antitumor drugs.

Physical Properties (referencing common similar derivatives): Usually a white or off-white crystalline powder, with a high melting point, soluble in some organic solvents (such as methanol, ethanol, dimethylformamide, etc.), and relatively low solubility in water.

Synthesis and Reaction Characteristics

Synthesis Route: It is often prepared from halogenated carboxylic acid esters and thiourea compounds through cyclization reactions. The reaction conditions are mild, and the product yield is high.

The amino and ester groups in the molecule have typical reactivity: the amino group can undergo acylation and diazotization reactions; the ester group can undergo hydrolysis and alcoholysis reactions, facilitating further structural modification.