Methyl 2-amino-3-thiophenecarboxylate

Methyl 2-amino-3-thiophenecarboxylate [4651-81-4] or 2-amino-3-carbomethoxythiophene or 2-amino-3-thiophenecarboxylic acid methylester is a white solid with the melting point of 72-73 °C.^[1]

Preparation of Methyl 2-amino-3-thiophenecarboxylate:

It can be prepared by modifed Gewald reaction^[2] using methyl cyanoacetate and 1,4-dithiane-2,5-diol in the presence of triethylamine in methanol. ^[3]

Application of Methyl 2-amino-3-thiophenecarboxylate:

2-Aminothiophene derivatives are important five-membered building blocks in organic synthesis. Urea derivatives of 2-amino-3-carbomethoxythiophene exhibited promising in vitro cytotoxicity against a human cancer cell lines as an effective binders of ribonucleotidereductase protein.^[4] It was used as a building block in synthesis of various thienopyrimidine derivatives which are  interesting structural element in development of pharmaceutical compounds.^[5] Among others, these heterocycles have been used as part of kinase inhibitors to regulate dysfunctional cell signalling in cancer cells,^[6] as calcium receptor antagonists,^[7] transglutaminase inhibitors,^[8] as peptidase IV inhibitors^[9] and against hepatitis C virus infections.^[10]

Product categorization (Chemical groups):

Main category:

• Amines / Amine salts / Imines
• Carboxylic acid esters / Lactones

Second level:

• Aromatic compounds

Third level:

• Thiophene derivatives

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