Uses
Ethyl 2-Amino-1,3-thiazole-4-carboxylate is a chemical reagent used in the preparation fo SAR thiazolamino arylaminopyrimidines as anaplastic lymphoma kinase inhibitors. As well as in the synthesis of 4-bicyclick piperadine derivatives as potent stearoyl-CoA desaturase (SCD1) inhibitors in the treatment of cancer.
Synthesis
GENERAL METHOD: A mixture of thiourea (1.2 mmol) and ethyl 3-bromopyruvate (1 mmol) in ethanol (2 mL) was reacted with stirring at 70°C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and subsequently poured into ice water. The precipitate precipitated was collected by filtration and dried to give the target product ethyl 2-aminothiazole-4-carboxylate. The products were characterized as follows: 6a (99% yield), white solid, melting point 150-152 °C (literature value 149-150 °C); 6b (100% yield), white solid, melting point 162-165 °C (literature value 163-164 °C); 6c (0.236 g, 93% yield), white solid, melting point 179-181 °C (literature value 180- 181°C); 6d (98% yield), white solid, melting point 203.6-204.2°C (literature value 204.0-204.5°C); 6e (94% yield), bright yellow solid, melting point 287-288°C (literature value 285-286°C); 6f (100% yield), white solid, melting point 172-174°C (literature value 172°C).
References
[1] Arkivoc, 2018, vol. 2018, # 7, p. 110 - 118
[2] Patent: CN104016944, 2016, B. Location in patent: Paragraph 0014-0015; 0040-0041
[3] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 5764 - 5768
[4] Letters in Drug Design and Discovery, 2018, vol. 16, # 2, p. 160 - 173
[5] Patent: WO2007/146066, 2007, A2. Location in patent: Page/Page column 151-152
