The origin of a common compound about Imidazo[1,2-a]pyridine-2-carboxylic acid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Electric Literature of 64951-08-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 64951-08-2 as follows.

Step (d) N-[4-(l-cyclopentyl-6-fluoro-2,4-dioxo-l,4-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)cyclohexyl]imidazo[l,2-a]pyridine-2-carboxamide To a mixture of imidazo[l,2-a]pyridine-2-carboxylic acid (89mg, 0.55mmol), HATU(220mg, 0.55mmol), HOAT (75mg, 0.55mmol) and 3-(4-aminocyclohexyl)-l-cyclopentyl-6-fluoro-pyrido[2,3-d]pyrimidine-2,4(lH,3H)-dione hydrochloride (176mg, 0.46mmol) inN-methylpyrrolidinone (10ml) was added ethyl-di-isopropylamine (0.31ml, 1.81mmol) over a period of 20 seconds. Stirring was continued at ambient temperature for 3 days and the reaction mixture was poured onto water. The obtained solid was filtered, dried on the sinter, dissolved in chloroform and adsorbed onto silica gel. Flash chromatography using a mixture of petrol ether and ethyl acetate yielded the title compound (55mg, 24%) as a colourless solid.1H NMR (300MHz, DMSO-J*): delta 8.77 (IH, d); 8.60 (IH, ddd); 8.40 (IH, s); 8.25 (IH, dd); 7.78 (IH, d); 7.68 (IH, d); 7.38 (IH, dd); 7.00 (IH, dd); 5.80 (IH, p); 4.84 (IH, bt);2.89 (IH, bs); 2.50 – 2.70 (2H, bm); 2.04 – 2.22 (2H, bd); 1.41 – 2.04 (12H, m).APCI-MS m/z: 491 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem