4-IODO-PYRIDIN-3-YLAMINE

3-amino-4-iodopyridine is an aminopyridine that is 3-aminopyridine carrying an additional iodo substituent at postion 4. It has a role as a Saccharomyces cerevisiae metabolite. It is an aminopyridine and an organoiodine compound.

iV-(4-Iodo-pyridin-3-yl)-2, 2-dimethyl-propionamide (20.00 g, 65.76 mmol) was charged to a 2 L round-bottom flask and 24percent sulfuric acid in water (640 mL) was added carefully. The mixture was heated to 100 °C for 4 hours. The reaction was determined complete by analyitical HPLC. The mixture was allowed to cool to room temperature and then carefully adjusted to pH 7-8 with 4Ν NaOH (approximately 700 mL). Saturated sodium bicarbonate was added to the mixture and the product extracted into dichloromethane (3 X 500 mL). The organic layers were combined and concentrated to give 3-amino-4-iodo- pyridine (13.3 g, 92percent).The product of preparation 22 (4.69g, 15.4mmol) and dilute sulphuric acid (24percent, 120mL) were heated under reflux for 1 hour. The reaction was performed according to a procedure in the literature (Tetrahedron Lett. 2005, 46, 6363). A 1 L three-neck round-bottom flask was equipped with a mechanical stirrer, thermocouple, nitrogen inlet, and drying tube and placed in a heating mantle. The flask was charged with N-(4-iodo(3-pyridyl))-2, 2-dimethylpropanamide (43, 45 g) and 25percent sulfuric acid (270 mL). The solubility of starting material in 25percent sulfuric acid was very high and formed light yellow clear solution. The reaction mixture was heated to 80° C. for 8 h. The reaction mixture was stirred continually at 80° C. until deemed to be complete, i.e., upon complete disappearance of starting material (N-(4-iodo(3-pyridyl))-2, 2-dimethylpropanamide, 43). If reaction was not complete, stirring was continued at 80° C. for additional 6 h then monitored again, and repeated until complete. Typically, reaction was complete within 4-6 h. The reaction was monitored by TLC (SiO

Molecular Weight:220.01
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:219.94975
Monoisotopic Mass:219.94975
Topological Polar Surface Area:38.9
Heavy Atom Count:8
Complexity:76.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes