ETHYLIMIDAZO[1,5-A]PYRIDINE-3-CARBOXYLATE

A solution of ethyl [(pyridin-2-ylmethyl)carbamoyl]fonTlate (1.00 g, 4.80 mmol, 1.00 equiv) and phosphorus pentoxide (3.41 g, 24.02 mmol, 5.00 equiv) in phosphorus oxychloride (30 mL) was stirred for 5 h at 110 °C. The resulting mixture was concentrated under vacuum. The residue waspurified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:1). This resulted in 635 mg (70percent) of the title compound as a yellow solid. LC-MS (ES, m/z): 191 [M+H] .A solution of ethyl oxo[(pyridin-2-ylmethyl)amino]acetate (40 g, 192 mmol) in POCl2-(Aminomethyl)pyridine (1.5 g, 13.9 mmol) and pyridine (3.62 g, 45.8 mmol) were dissolved in CH2Cl2 (20 mL), and the solution was cooled by using an ice bath. A solution of ethyl oxalyl chloride (1.89 g, 13.9 mmol) in CH2Cl2 (10 mL) was added dropwise at 0 to –5 °C. After addition, the mixture was stirred for 2 h and a solution of TFAA (3.06 g, 14.6 mmol) in CH2Cl2 (10 mL) was added dropwise at –15 to –10 °C (ice-salt bath). The reaction mixture was allowed to stand overnight in the bath, then washed with sat. aq NaHCO3, and the CH2Cl2 layer was dried over Na2SO4 and concentrated. Yield: 2.4 g (91percent); white solid; mp 80 °C (Lit. [13] 80 °C). The 1H and 13C NMR spectroscopic data were identical to those reported previously. [4, 14, 18]

Molecular Weight:190.20
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:190.074227566
Monoisotopic Mass:190.074227566
Topological Polar Surface Area:43.6
Heavy Atom Count:14
Complexity:220
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes