The synthetic route of 106961-33-5 has been constantly updated, and we look forward to future research findings.
Adding a certain compound to certain chemical reactions, such as: 106961-33-5, N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, 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, Recommanded Product: 106961-33-5, blongs to pyridine-derivatives compound. Recommanded Product: 106961-33-5
Step (ii): Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a|pyridine-3- acetonitrile (10)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-N,N- dimethylmethylamine (8) ( (230 grams, 0.82 mmol) (obtained from step (i)) in dichloromethane (600 mL) under stirring. Cooled the above solution to 0 – 5 0C, add ethylchloroformate (98.4 grams, 0.90 mmol) slowly over a period of 30 minutes. Stirred the above reaction mass for a period of 45 minutes at the same temperature, distilled off the solvent under reduced pressure, which produced 332 grams crude carbamate salt of dimethylaminomethyl imidazopyridine (2) as yellow colored solid. Dissolved the obtained solid immediately in water (690 mL), basify the solution to pH 7.5-8.0 using 10% sodium hydroxide solution. Added sodium cyanide (48.4 grams, 0.99 mmol) to the above reaction mass and stirred at 50 – 55 0C for a period of 3 hours. Cooled the above reaction mass to room temperature, extracted the solution with chloroform (300 mL, 2×200 mL). Combined organic layers and washed with water (500 mL) and brine (400 mL). Dried with anhydrous sodium sulfate, filtered and concentrated the solution until the volume reaches to 250 mL. Add methanol (1000 mL), stirred for the period of 30 minutes. Filtered the formed off white solid from the solution and dried in the oven until constant weight reached. Dry weight of obtained 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile(10) is 165.0 grams. Yield: 76% Purity: 96%Melting Range: 176.9 – 178.00C;IR spectra (cm”1): 2921, 2895, 2249, 1500, 1386, 1343, 824, 799;1H NMR (400 MHz, CDCl3): delta 2.42(s, 6H), 4.13 (s, 2H), 7.16 (dd, J= 9.1 Hz, J= 1.5 Hz, IH), 7.31 (d, J= 7.9 Hz, 2H), 7.58 (d, J= 8.0 Hz, 2H), 7.60 (d, J= 9.6 Hz, IH), 7.80(s, IH);Mass (m/z): 262.5 (M+H)+; Example 2:Preparation of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- acetic acid (12)Dissolved the 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine (9) (100 grams, 0.45 mmol) in acetic acid (500 mL) under stirring. Cooled the reaction mass to 5 – 10 0C, added 40% aqueous solution of dimethylamine (76 grams) slowly, followed by addition of paraformaldehyde (17.7 grams). Stirred the reaction mass at 50 – 55 0C for the period of 3 hours and removed acetic acid under reduced pressure. Added water (1000 mL), basify the solution (pH 8.0) by adding 30% sodium hydroxide solution. Extracted the solution with dichloromethane (3×300 mL), washed the organic layer with water (500 mL) and brine solution (500 mL). Dry with anhydrous sodium sulfate, filtered and distilled the solvent until the volume reaches to around 300 mL. This solution contains 6-methyl-2-(4-methylphenyl)imidazo[l ,2-a]pyridine-3-N,N- dimethylmethylamine (10), 89% purity by HPLC, and used further as it is. Cooled the above organic solution to 0 – 5 0C, added ethylchloroformate (58.3 grams, 0.54 mmol) slowly over a period of 30 minutes. Stirred the reaction mass for one hour at the same temperature, distilled off the solvent under reduced pressure to obtain carbamate salt as bright yellow colored solid (2). This solid was dissolved in water (300 mL), basified the solution to pH 7.5 – 8.0 using 10% sodium hydroxide solution. Added sodium cyanide (26.5 grams, 0.54 mmol) and stirred the reaction mass at 50 – 55 0C for a period of 3 hours. Cooled the reaction mass to room temperature and filtered the yellow solid and washed with water (500 mL). This crude solid contains 6- methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3-acetonitrile (10), 82% purity by HPLC, and used for hydrolysis without any further purification. The above crude solid was dissolved in 50% sulfuric acid (624 mL), refluxed the reaction mass at 110 0C for 4 hours. Cooled the reaction mass to room temperature and added to a flask contain of ice cold water (2.5 L). Basified the white ppt solution by adding sodium hydroxide flakes portion wise until pH 9.0. Extracted the solution with dichloromethane (2 x 300 mL) and discarded. Added carbon (5.0 grams), stirred for 30 minutes and filtered through a pad of celite. Acidified the solution pH 5.5 by adding glacial acetic acid and obtained white solid filtered. Filtered cake was washed with water (500 mL) and dried in the airflow oven at 60 – 65 0C until constant weight reached. 78.0 grams of 6-methyl-2-(4-methylphenyl)imidazo[l,2-a]pyridine-3- aceticacid (12) obtained as off-white solid. Yield: 62.0% Purity: 99.5 %Melting Range: 234.0 – 235.20C; IR spectra (cm 1): 3427, 2919, 1701, 1508, 1183, 827, 805; 1H NMR (400 MHz, DMSO-c4): delta 2.31 (s, 3H), 2.34 (s, 3H), 4.08 (s, 2H), 7.17 (dd, J=9.1 Hz, J= 1.5 Hz, IH), 7.28 (d, J= 8.0 Hz, 2H), 7.51 (d, J= 9.1 Hz, IH), 7.61 (d, J= 8.0Hz, 2H), 8.22 (s, lH);Mass (m/z): 281.2 (M+H)+
The synthetic route of 106961-33-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; WO2009/7995; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem