Application of 66909-30-6, 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 66909-30-6 as follows.
6-(4-(2-Chloro-5-methylnicotinamido)benzoyl)-W-(2-fluoro-6-methylphenyl)-5,6-di hydro-4H-benzo[i)]thieno[2,3-c ]azepine-2-carboxamide; Intermediate (Ilia). Oxalyl chloride (133 mL, 1.58 mol) was added to a suspension of 2-chloro-5-methyl nicotinic acid (225.4 g, 1.313 mol) in DCM (2254 mL) at 18-25C followed by DMF (0.8 mL, 0.010 mol) (results in mild exotherm and gas evolution) and the reaction stirred at 20-25C for 1 hr. HPLC analysis of an aliquot (quenched into methanol) indicated <1 % of 2-chloro-5- methylnicotinic acid was remaining. The solvent was removed in vacuo and the oily residue was azeotroped with DCM (500 mL) to remove residual oxalyl chloride. The resulting oil was taken up into DCM (413 mL) and was added dropwise over 10 min to a suspension of 6-(4-aminobenzoyl)-/V-(2-fluoro-6-methylphenyl)-5,6-dihydro-4/-/-benzo[ 5] thieno[2,3-d]azepine-2-carboxamide (412.9 g, 0.876 mol) in a mixture of pyridine (283 mL, 3.502 mol) and DCM (28920 mL) whilst maintaining the internal temp <40C (maximum temp reached 38C). The reaction was stirred at 18-25C for 1 hr after which time HPLC (sample quenched into methanol) indicated the reaction was complete (<1 % of aniline s/m remaining). Heptane (3300 mL) was added to the mixture at 18-25C and the resulting suspension was stirred for 15 min and the solids then collected by filtration. The filter cake was washed with heptane (2 x 1650 mL) and the crude solid so obtained was slurried in water (4130 mL) at 90- 95C for 30 min and then cooled to 18-25C.The solids were collected by filtration, washed with water (2 x 826 mL) and dried in a vacuum oven at 50C to give the title compound as a white solid (504.2 g, 92% active yield, HPLC purity [230 nm] 98.24%; containing 0.3% pyridine HCI by 1 H NMR and 0.4%. H20 by KF); R< 12.19 min; m/z 625.6 (M+H)+ (ES+).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66909-30-6, its application will become more common.
Reference:
Patent; PULMOCIDE LIMITED; HUNT, Simon Fraser; ONIONS, Stuart Thomas; SHERBUKHIN, Vladimir; FORDYCE, Euan Alexander Fraser; MURRAY, Peter John; BROOKES, Daniel William; ITO, Kazuhiro; STRONG, Peter; (51 pag.)WO2016/55791; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem