Month: April 2022

Reference of 700811-29-6, 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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine. A new synthetic method of this compound is introduced below.

A microwave reaction vessel was charged with 1.34 g of (2-Chloro-pyridin-4-yl)-hydrazine (7.48 mmol, 1.1 equiv) and 2.00 g of N-cyano-N’-(4-acetamidophenyl)-O-phenylisourea (6.80 mMol, 1 equiv). The solids were dissolved in 40 mL of NMP and 8 mL of DIEA. The sealed vessel was warmed to 220 C. for 6 min via microwave irradiation. Upon cooling, the resulting solution was poured into 200 mL of saturated sodium bicarbonate. The precipitate was collected and washed with 3×100 mL of water. After azeotropic drying (3×50 mL of acetonitrile) the dark yellow solid (2.0 g, 5.80 mMol, 85% yield) was used without further purification. 1H NMR (500 Mhz, DMSO-d6) delta 9.68 (1 H, s), 9.00 (1 H, s), 8.40 (1 H, d), 7.67 (2 H, m), 7.50 (2 H, d), 7.40 (2 H, d), 6.95 (2 H, s), 2.0 (3 H, s) ppm. LCMS: 2.16 minutes/343.95 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,700811-29-6, 2-Chloro-4-hydrazinopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Salituro, Francesco; Ledeboer, Mark; Ledford, Brian; Wang, Jian; Pierce, Albert; Duffy, John; Messersmith, David; US2006/63756; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74134-42-2 , The common heterocyclic compound, 74134-42-2, name is 2-Bromo-6-(methylthio)pyridine, molecular formula is C6H6BrNS, 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.

2-Bromo-6-(methylthio)pyridine (1.00 g, 4.90 mmol) and trifluoroacetamide (0.831 g, 7.35 mmol) in THF (10 mL) was added dropwise to a pre-cooled suspension of sodium hydride (60% in mineral oil) (0.176 g, 4.41 mmol) in THF (5 mL) at 0 00 under nitrogen. After 5 mm, a solution of 1,3-dibromo-5,5- dimethylhydantoin (2.10 g, 7.35 mmol) in THF (7.5 mL) was added dropwise. After 1 h, the reaction mixture was partitioned between EtOAc and 25% sodium sulfite (aq) solution, separated, extracted (EtOAc x 2), dried (Phase Separator), and the solvents were removed in vacuo to give the title compound as a colourless oil that turned into a white solid on standing. The material was carried through to the next step without further purification.LCMS (Method A): RT = 1.02 mi mlz = 315, 317 [M+H]

The synthetic route of 74134-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BURKAMP, Frank; ROUNTREE, James Samuel Shane; TREDER, Adam Piotr; (155 pag.)WO2018/11569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid, molecular formula is C7H6N2O4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 2-Methyl-5-nitro-3-pyridinecarboxylic acid

A mixture of intermediate C (14 mg, 0.06 mmol), oxalyl chloride (0.3 mmol) and a catalytical amount of DMF in 1 ml DCM was stirred at r.t. for 1.5 hr. After evaporation to dryness, the resulting acid chloride was coupled with compound 17 (0.05 mmol) in 0.5 ml DCM in presence of DIEA (44 mul, 5 eq.). The reaction mixture was stirred at r.t. overnight before concentration to dryness. Preparative HPLC purification gave 28.3 mg of the product as the TFA salt. (Calculated mass: 552.6, observed mass: 552.8).

With the rapid development of chemical substances, we look forward to future research findings about 59290-81-2.

Reference:
Patent; KEMIA, INC.; WO2007/56016; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 121643-44-5, 2-Methoxy-3-(trifluoromethyl)pyridine, 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: 121643-44-5, blongs to pyridine-derivatives compound. Recommanded Product: 121643-44-5

2. 3-Trifluoromethyl-pyridin-2-ol EPO Heat a mixture of 2-methoxy-3-trifluoromethyl-pyridine (1.0 g, 5.6 mmol) and 30% HBr in acetic acid (5 mL) at reflux for 1 hour. Cool the mixture and remove the volatiles by rotary evaporation. Add ether and collect the precipitate by filtration. Air-dry to give the title compound as the hydrogen bromide salt.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,121643-44-5, 2-Methoxy-3-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/42289; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1018505-59-3, 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 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation of 6-bromo-5-ethyl-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine A mixture of 5-(4-ethylpiperazin-1-yl)pyridin-2-amine (3.30 g, 16.0 mmol), 6,8-dibromo-5-ethylimidazo[1,2-a]pyridine (5.00 g, 16.4 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (2.14 g, 3.44 mmol) and cesium carbonate (16.4 g, 50.5 mmol) in 1,4-dioxane (200 mL) was sparged with nitrogen while stirring for 10 min. Palladium(II) acetate (368 mg, 1.51 mmol) was then added and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted with a mixture of 1:1 methanol/methylene chloride (200 mL) and filtered through a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1:24 methanol/methylene chloride to 2:23 methanol/methylene chloride) to afford 6-bromo-5-ethyl-N-(5-(4-ethylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-8-amine as a brown solid: 1H NMR (400 MHz, CDCl3) d 8.40 (s, 1H), 8.03 (d, J=2.8 Hz, 1H), 7.76 (s, 1H), 7.54 (s, 2H), 7.28-7.25 (m, 1H), 6.84 (d, J=9.2 Hz, 1H), 3.18-3.13 (m, 4H), 3.10 (q, J=7.6 Hz, 2H), 2.64-2.60 (m, 4H), 2.49 (q, J=7.2 Hz, 2H), 1.28 (t, J=7.6 Hz, 3H), 1.13 (t, J=7.2 Hz, 3H).

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); A1;,
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. 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Chloro-3-methylpyridine-2-carboxylic acid

Example 170 Synthesis of N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-chloro-3-methylpicolinamide The titled compound was synthesized by procedure and steps analogous to those described in Method Y, Example 163 above, but using 5-chloro-3-methyl-pyridine-2-carboxylic acid (Frontier Scientific, Inc) in step 10. MS m/z=463.0 [M+H]+. Calculated for C19H16ClF5N4O2: 462.8 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.68 (br. s., 3H) 1.94 (t, J=12.52 Hz, 1H) 2.78 (br. s., 4H) 3.99-4.15 (m, 1H) 7.03 (br. s., 1H) 7.66 (br. s., 1H) 8.11 (br. s., 1H) 8.39 (br. s., 1H) 10.06 (br. s., 1H)

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, 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 116855-03-9, name is 3-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine, molecular formula is C7H6BrN3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 3-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine

Example 26b [0789] [0790] 3-bromo-1-methyl-pyrazolo[3,4-b]pyridine (100 mg, 0.472 mmol) is dissolved in toluene (5 mL) and tributyl(1-ethoxyvinyl)tin (187 mg, 0.519 mmol) and tetrakis(triphenylphosphine) palladium(0) (54 mg, 0.047 mmol) are added to the solution and the reaction is refluxed for 2 h. Volatiles are evaporated under reduced pressure and the resulting residue is suspended in THF/aqueous 2M HCl 1:1 and stirring is continued for 1 h. The reaction mixture is basified with Na2CO3 saturated solution, and extracted with ethyl acetate. The organic layer is dried, evaporated and the resulting residue is purified by flash chromatography (eluent 0-100% EtOAc/Cyclohexane) to give the title compound (70 mg, 85%) [0791] UPLC-MS (Method 2): Rt=0.78 min [0792] MS (ESI pos): m/z=176 (M+H)+

With the rapid development of chemical substances, we look forward to future research findings about 116855-03-9.

Reference:
Patent; Boehringer Ingelheim International GmbH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; US2014/343065; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188637-63-0, 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 188637-63-0 as follows.

To a mixture of A214.2 (14.3 g, 76.5 mmol) and pyridine (14.3 mL) in anhydrous tetrahydrofuran (250 mL) was added acetic anhydride (14.3 mL), and the reaction mixture was stirred for 3 hr at room temperature. The solvent was removed under reduced pressure, and the oily residue was diluted with dichloromethane, washed with water, washed with a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. Concentration followed by drying under reduced pressure afforded 16.3 g (93%) of A214.3 as an off-white solid. The compound had an HPLC retention time = 0.987 min. (Column: Chromolith SpeedROD 4.6 x 50 mm – 4 min.; Solvent A = 10% MeOH, 90% H2O, and 0.1% TFA; Solvent B = 90% MeOH, 10% H2O, and 0.1% TFA) and a LC/MS M+1 = 229.10 and 231.10.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188637-63-0, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 1149-24-2

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

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, 1149-24-2, Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 127356-38-1, 2-Methoxy-5-nitropyridin-4-amine, 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, 127356-38-1, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Methoxy-5-nitropyridin-4-amine

Step 3: Synthesis of 6-methoxypyridine-3,4-diamine Aq. conc. HCl (1 ml, 32.9 mmol) was diluted with water. To the solution was added tin (II) chloride (0.448 g, 2.365 mmol), followed by 2-methoxy-5-nitropyridin-4-amine (0.1 g, 0.591 mmol). The mixture was heated to 60 C. for 18 h. The reaction mixture was cooled to room temperature, then basified using 10% NaOH solution. The mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude compound was triturated with 10% ethyl acetate in Pet-ether to afford 6-methoxypyridine-3,4-diamine (0.06 g, 0.366 mmol, 62.0% yield) as a solid. 1H NMR (400 MHz, DMSO-d6): delta ppm 7.21 (s, 1H), 5.83 (s, 1H), 5.39 (b s, 2H), 4.04 (b s, 2H), 3.62 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,127356-38-1, its application will become more common.

Reference:
Patent; Sun, Li-Qiang; Zhao, Qian; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshim, Pulicharla; Gillis, Eric P.; Scola, Paul Michael; US2014/127156; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem