Extracurricular laboratory: Synthetic route of tert-Butyl (3-formylpyridin-4-yl)carbamate

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116026-93-8, tert-Butyl (3-formylpyridin-4-yl)carbamate, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 116026-93-8, tert-Butyl (3-formylpyridin-4-yl)carbamate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, name: tert-Butyl (3-formylpyridin-4-yl)carbamate, blongs to pyridine-derivatives compound. name: tert-Butyl (3-formylpyridin-4-yl)carbamate

Example 106: (5Z)-5-[(4-aminopyridin-3-yl)methylidene]-2-(piperidin-l-yl)-4,5-dihydro- l,3-thiazol-4-one hydrochloride; (3-Formyl-pyridin-4-yl)-carbamic acid tert-butyl ester (490mg, 1.5mmol), piperidine (0.30 mL, 3.0 mmol), and rhodanine (203mg, 1.5mmol) were added into 10 mL of ethanol in 5OmL flask. The resulting mixture was heated at 75 0C overnight. The solvent was evaporated, 0 and the crude was purified by flash chromatography (0 to 10% MeOH in DCM gradient). 200 mg of [3 -(4-Oxo-2 -piperidin-l-yl-4H-thiazol-5-ylidenemethyl)-pyridin-4-yl]-carbamic acid tert- butyl ester yellow solid was collected as pure product (yield 34%).[3-(4-Oxo-2-piperidin- 1 -yl-4H-thiazol-5-ylidenemethyl)-pyridin-4-yl]-carbamic acid tert- butyl ester (200mg) was dissolved in 5mL of methanolic HCl (4M). The resulting mixture was 5 stirred at room temperature for 2 hours. The solvent was evaporated, and the remaining solid was dried under vacuum to provide desired product (yield 99%). 1H NMR (400 MHz, DMSO- d6) delta 1.67 (m, 6H), 3.5 (m, 2H), 3.90 (m, 2H), 6.97(d, IH), 7.50 (s, IH), 8.13(d, IH), 8.30 (s, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116026-93-8, tert-Butyl (3-formylpyridin-4-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; CHLORION PHARMA, INC.; WO2009/97695; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem