Chemical Properties
white to light yellow crystal powde
Uses
4-Methylthiazole-5-carboxylic acid is used as a reagent to synthesize thiazolylimidazolidinone compounds that act as Stearoyl-CoA desaturase-1 (SCD1) inhibitors. These SCD1 inhibitors are used in the treatment of metabolic diseases. 4-Methylthiazole-5-carboxylic acid is also used as a reagent to synthesize 4-Methyl-5-formylthiazole, an important intermediate in the synthesis of Cefditoren pivoxil (C242700).
Definition
ChEBI: 4-Methyl-thiazole-5-carboxylic acid is an aromatic carboxylic acid and a member of thiazoles.
Synthesis
A mechanical stirrer, thermometer and constant pressure dropping funnel were assembled in a 10 L glass reactor and 1 mole of phosphorus pentasulfide (P4S10) and 6 kg of ethylene glycol dimethyl ether were added as solvent under nitrogen protection. Under stirring conditions, 5 moles of formamide was slowly added dropwise and the reaction lasted for 2 hours. Subsequently, 5 moles of ethyl 2-chloroacetoacetate was added dropwise and the reaction was carried out at room temperature for 608 hours. Upon completion of the reaction, the reaction mixture was cooled to 10 °C and the white solid product was collected by filtration. The solid product was dissolved in 4 times its weight in water and the pH was adjusted to 7-8 with 20% sodium hydroxide solution. filtration at 0-5 °C gave ethyl 4-methylthiazole-5-carboxylate as a white solid with 99% purity and 95.8% molar yield.
References
[1] Patent: CN105130924, 2017, B. Location in patent: Paragraph 0021; 0022
