Preparation and application background and overview of 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride
2-Amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride is an organic intermediate that can be synthesized from N-tert-butoxycarbonyl-4-piperidone Prepared in two steps.
Preparation and application of 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride
Preparation and application step 1 of 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride,
Mix N-tert-butoxycarbonyl-4-piperidone (100.00g, 501.98mmol) with sulfur (32.19g, 1.00mol) and cyanamide (42.20g, 1.00mol) in 300mL pyridine, and heat to 130°C, react for 1.5h, then cool to 20°C, filter, wash with ethyl acetate, and dry to obtain a light yellow solid product 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine- 5(4H)-tert-butyl formate (80g, yield 60.55%);
Preparation and application step 2 of 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride,
Dissolve formylphenylboronic acid 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylic acid tert-butyl ester in dichloromethane solution, add dihydrogen chloride Oxyhexacyclic solution, stir at room temperature for 1.5h to obtain 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride.
Preparation and application of 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride
WO 2010125799 reported that 2-amino-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine hydrochloride can be used as a pharmaceutical intermediate nitropyridine for the preparation of PI3K inhibitors. The structure is shown in the figure below. As an important signaling pathway in cells, the PI3K/Akt/mTOR signaling pathway plays important biological functions in cell growth, survival, proliferation, apoptosis and other processes. However, disorder of this pathway can cause a series of diseases. Including diseases such as cancer, immune system and hematopoietic system. Relevant studies have shown that PI3K, a key regulatory site on this pathway, is closely related to the occurrence and development of tumors. Therefore, inhibiting the activity of PI3K has become one of the important strategies for the current development of anti-tumor drugs.
