Day: April 19, 2022

Adding a certain compound to certain chemical reactions, such as: 52687-85-1, Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride, 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: Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride, blongs to pyridine-derivatives compound. Recommanded Product: Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride

EXAMPLE 1 STR11 A mixture of 341 g (2 mols) of imidazo[1,2-a]pyridin-2(3H)-one hydrochloride and 700 ml of water is treated with portions of a solution of 80 g (2 mols) of sodium hydroxide in 200 ml of water, with stirring. A solution of 250.7 g (2.16 mols) of maleic acid in 600 ml of water is then added dropwise in such a way that the internal temperature of the reaction mixture remains between 40 C. and 45 C. After 30 hours at room temperature (20-25 C.), the mixture is cooled to 5 C., the precipitate formed is filtered off, the filtrate is concentrated to about half its volume in vacuo, and the product which has precipitated is filtered off with suction. The combined residues are washed with a small amount of cold methanol and dried at 50 C. in vacuo. This gives 400 g of 3-(1,2-dicarboxyethyl)-imidazo[1,2-a]pyridin-2(3H)-one with a melting point of 193 (decomposition).

The synthetic route of 52687-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4480106; (1984); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., name: Imidazo[1,2-a]pyridine-2-carboxylic acid

Step (a) tert-butyl {cis-4-[(imidazo[l,2-a]pyridin-2- ylcarbonyl)amino] cyclohexyl} carbamate, O Imidazo[l,2a]pyridine-2-carboxyli acid (5 g, 30.8 mmol) was dissolved in NMP (200 ml) and DIEA (11.96 g, 16.43 ml) was added, followed by O-(7-Azabezotriazol-l-yl)- N,N,N’,N’-tetramethyluronium hexafluorophosphate (14.07 g, 37 mmol). The reaction was stirred for 5 min. (4-Amino-cyclohexyl)-carbamic acid tert-butyl ester (6.61 g, 30.8 mmol) was then added and the solution stirred at room temperature ovenight. Water was added and the product extracted with ethyl acetate. The organic phase was dried (anhydrous magnesium sulphate), filtered and concentrated in vacuo to afford the sub-title compound (8.5 g, contains some NMP). This was used without further purification. APCI (+ve) m/z: 359 [M+H]

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid.

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

Related Products of 107867-51-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: A mixture of compound 1.2 (0.2 mmol) and thiocarbonyldiimidazole (0.2 mmol) in dry THF (2.0 mL) was stirred at room temperature for 30 minutes under an atmosphere of N2. 5-Trifluoromethyl-pyridine-2,3-diamine (0.2 mmol) was added and the reaction stirred at room temperature until the reaction was deemed complete. The reaction mixture was then treated with N,N’-dicyclohexylcarbodiimide (0.2 mmol) and the resulting mixture was stirred at 40-60 C. for several hours. The solvent was removed and the residue was purified by preparative HPLC to give the titled compound. 1H NMR (CD3OD, 400 MHz): delta 8.76 (s, 1H), 8.51 (s, 1H), 8.38 (s, 1H), 7.95 (s, 1H), 7.56 (d, J=7.3 Hz, 2H), 7.48 (s, 1H), 7.38 (d, J=6.4 Hz, 2H), 4.03 (s, 2H), 3.09 (s, 2H) ppm; EIMS (m/z): 456.1 (M++H).

According to the analysis of related databases, 107867-51-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lew, Willard; Baskaran, Subramanian; Oslob, Johan D.; Yoburn, Joshua C.; Zhong, Min; US2006/35908; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22918-01-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.22918-01-0, name is 2-Bromo-4-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.441, as common compound, the synthetic route is as follows.

Preparation of 2-bromo-3-methyl-4-chloro-pyridine To a solution of 2,2,6,6-tetramethyl-pyridine (21.1 mL, 125 mmol) in freshly distilled THF (120 mL) at -78C was added nBuLi (50 mL, 125 mmol) in 30 min. The resulting mixture was stirred at -78C for 30 min and was added through a cannula over 30 min to a solution of 3-bromo-4-chloro-pyridine (20.0 g, 104 mmol) in freshly distilled THF (60 mL) that had been cooled to -78C prior to the addition. The reaction mixture was stirred at -78C for 30 min before iodomethane (7.78 mL, 125 mmol) was added over a period of 10 min. The reaction was stirred at -78C for 30 min and was allowed to warm up to room temperature prior to be quenched with aqueous NH4Cl (65 mL). The aqueous phase was extracted with ethyl acetate (2X150 mL). The organic phases were separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 5:1) to afford the title compound as a yellow solid (10.6 g, 49%). 1H NMR (CDCl3, 300 MHz) delta ppm: 8.10 (d, J = 5.1 Hz, 1 H), 7.27 (d, J = 5.1 Hz, 1H), 2.51 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 22918-01-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Emergent Product Development Gaithersburg Inc.; Roussel, Patrick; Heim, Jutta; Schneider, Peter; Bartels, Christian; Liu, Yaoquan; Dale, Glenn; Milligan, Daniel; (107 pag.)EP3034078; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 186203-81-6, tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of tert-but l hexahydro- l H-pyrrolo[3,4-b]pyridine-6(2H)- carboxylate (1.60 g), l -bromo-3-chloropropane (1.50 mL) and 2C03 (3.00 g) in acetone was heated to reflux for 9 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1 : 1 (v/v) PE/EA) to give the title compound as yellow oil (0.53 g, 65.00 %), HPLC: 89.00 %. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 303.2 (M+l ).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,186203-81-6, tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Jiancun; ZHANG, Yingjun; ZHANG, Weihong; LIU, Bing; ZHANG, Jiquan; LIU, Jinlei; ZHANG, Lu; WO2013/71697; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 184416-84-0, name is 2,3-Dichloroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 184416-84-0

2,3-Dichloro-isonicotinic acid methyl ester[00197] To a suspension of 2,3-dichloro-isonicotinic acid (7.7 g, 40 mmol) in dichloromethane (45 mL) were added DMF (0.1 mL) and oxalyl chloride (17.5 mL, 200 mmol). The reaction mixture was stirred at room temperature for 18 hours and then concentrated under reduced pressure. The resultant residue was azeotroped with toluene, then cooled to 00C and dissolved in methanol (135 mL). The mixture was allowed to warm to room temperature and then concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate and the resulting solution was washed with a saturated solution of sodium hydrogen carbonate, water and brine, dried (Na2SO4), filtered and concentrated to give the title compound as a colourless oil that crystallised on standing (7.9 g, 96%). 1H NMR (CDCl3, 400MHz) 8.38 (d, J = 5.0 Hz, IH), 7.52 (d, J = 5.0 Hz, IH), 3.99 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 184416-84-0.

Reference:
Patent; GENENTECH, INC.; WO2009/85980; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13958-93-5, Adding some certain compound to certain chemical reactions, such as: 13958-93-5, name is 3,5-Dichloroisonicotinic acid,molecular formula is C6H3Cl2NO2, 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 13958-93-5.

EXAMPLE 1A 3,5-Dichloroisonicotinamide A solution of 3,5-dichloro-isonicotinic acid (9.54 g, 49.6 mmol, commercially available form TCI) in benzene (100 mL) was treated with oxalyl chloride (8.7 mL), a catalytic amount of DMF (5 drops), stirred overnight at room temperature, and concentrated under reduced pressure. The residue was dissolved in diglyme (10 mL) and added dropwise to 35% NH2OH in water (150 mL). The mixture was filtered to provide 8.2 g of the title compound as a white powder. MS ((DCI (+)) m/e 190.9 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 13958-93-5, 3,5-Dichloroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dai, Yujia; Hartandi, Kresna; Michaelides, Michael R.; US2006/178378; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 99368-68-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine, molecular formula is C6H4ClF3N2, molecular weight is 196.5576, as common compound, the synthetic route is as follows.

(0876) Under ice-cooling, thionyl chloride (4 ml) was added dropwise over 20 minutes to water (27 ml). The mixture was stirred overnight for 12 hours to give a SO2 containing solution. Separately, Compound 288C (1.14 g) in dioxane (5 ml) was added to concentrated HCl (20 ml) at 0 C. The solution was stirred for 5 minutes. To this suspension/solution was added sodium nitrite (0.44 g) in water (6 ml) dropwise at 0 C. The solution was stirred at 0 C. for 3 hours. During this time, any solid formed was crushed with a glass rod to make sure that Compound 288C was completely reacted. To the SO2 containing solution was added copper(I) chloride (0.115 g). Then, to this solution was added the diazotized Compound 288C at 0 C. The solution was stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with 5% ethyl acetate in hexanes to provide the title compound.

The chemical industry reduces the impact on the environment during synthesis 99368-68-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AbbVie Inc.; Catron, Nathaniel; Lindley, David; Miller, Jonathan M.; Schmitt, Eric A.; Tong, Ping; US10213433; (2019); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 880870-13-3 ,Some common heterocyclic compound, 880870-13-3, molecular formula is C6H5BrClNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step 1: Preparation of l-(4-(6-chloro-4-methoxypyri din-3 -yl)phenyl)pyrrolidin-2-one. [0794] A mixture of l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin- 2-one (500 mg, 1.74 mmol), 5-bromo-2-chloro-4-methoxypyridine (387 mg, 1.74 mmol), Pd(dppf)Cl2 (127 mg, 0.174 mmol) and Na2C03 (554 mg, 5.22 mmol) in dioxane (6 mL) and water (1.5 mL) was degassed and purged w ith N2 for 3 times. And the resulting reaction mixture was stirred at 100 C for 2 hours under N2 atmosphere. A black suspension was formed. LCMS showed the purity of the desired product is 51% (Rt = 0.649 min; MS Calcd: 302.1; MS Found: 302.8 [M+H]+). The reaction mixture was diluted with water (10 mL). The aqueous layer was extracted with EtOAc (30 mL x3). The combined organic layer was washed with water (20 mL x2), brine (40 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by Combi Flash (20% to 60% EtOAc in PE) to give 1-(4- (6-chloro-4-methoxypyridin-3-yl)phenyl)pyrrolidin-2-one (450 mg, yield: 78%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,880870-13-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; KESICKI, Edward A.; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (450 pag.)WO2019/126731; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 878197-68-3, name is 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 878197-68-3

To a solution of Lambda/-methyl-5,6,7,8-tetrahydro-8-quinolinamine (500 mg, 3.1 mmol) and 5-bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (770 mg, 3.4 mmol) in dichloroethane (17 ml_) was added acetic acid (180 mul_, 3.1 mmol) and sodium triacetoxyborohydride (2.0 g, 9.3 mmol). The mixture was stirred at room temperature for 15 hours and then filtered through a silica plug and rinsed with 10% ammonium hydroxide- acetonitrile. The solvent was removed and the residue diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, and dried with magnesium sulfate to give 1.1 g (99% yield) of Lambda/-[(5-bromoimidazo[1 ,2-a]pyridin-2-yl)methyl]-Lambda/- methyl-5,6,7,8-tetrahydro-8-quinolinamine as an orange oil. 1H-NMR (CDCI3): delta 8.50 (d, 1H), 7.92 (s, 1 H), 7.49 (d, 1 H), 7.32 (d, 1 H), 7.03 (m, 2H), 6.96 (m, 1H), 4.09 (m, 1 H), 3.94 (s, 2H), 2.72 (m, 2H), 2.40 (s, 3H), 2.12 (m, 1H), 1.99 (m, 2H), 1.68 (m, 1H); MS m/z 372 (M+1).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 878197-68-3, 5-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/26703; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem