Pyridine-derivatives

Synthetic Route of 504-29-0, 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 504-29-0, name is Pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation 47 pyridine-2-amino-5-sulphonic Acid 2-Aminopyridine (80 g, 0.85 mol) was added portionwise over 30 minutes to oleum (320 g) and the resulting solution heated at 140 C. for 4 hours.. On cooling, the reaction was poured onto ice (200 g) and the mixture stirred in an ice/salt bath for a further 2 hours.. The resulting suspension was filtered, the solid washed with ice water (200 ml) and cold IMS (200 ml) and dried under suction to afford the title compound as a solid, (111.3 g). LRMS: m/z 175 (M+1)+.

According to the analysis of related databases, 504-29-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6407114; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 771579-27-2, 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. 771579-27-2, name is 3-(Aminomethyl)-4,6-dimethylpyridin-2(1H)-one, molecular formula is C8H12N2O, 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.

Carboxylic acid (13.44g, 39.4mmol) was dissolved in 70mLDMSO, and added with stirring 4,6-dimethyl-3-aminomethyl-pyridinePyridine -2 (1H) – one (12.4g, 81.9mmol). Stirred at room temperature 15min, then add hexafluorophosphate, benzotriazol-1-yl – yloxy tripyrrolidinophosphonium phosphorus (PYBOP) (31.9g, 61.4mmol), stirred at room temperature overnight, until the reaction was complete (developing solvent: ethyl acetate / ethanol = 5: 1), the reaction mixture was poured into 700mL ice water, stirred for 30min, to obtain a solid by suction filtration, washed with a 500 mL of water, and dried under vacuum dryer, the resulting solid was added with stirring acetonitrile (75mL × 2), suction, vacuum dryer. The resulting solid was combined with 100mL stirring methanol / dichloromethane (5:95), filtration, and dried under reduced pressure to obtain a solid product was thoroughly 14g, Yield 74%

According to the analysis of related databases, 771579-27-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu University of Technology; Liang, Guoping; Wang, Yazhen; Zheng, Chunzhi; Zhao, Dejian; Zhang, Jizhen; (13 pag.)CN105440023; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 98549-88-3, 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.98549-88-3, name is 1H-Pyrrolo[2,3-b]pyridin-5-ol, molecular formula is C7H6N2O, molecular weight is 134.14, as common compound, the synthetic route is as follows.

Example 724-[4-(1H-Pyrrolo[2,3-b]pyridin-5-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; A mixture of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 50 mg, 0.15 mmol), 1H-pyrrolo[2,3-B]pyridin-5-ol (Matrix Scientific, Columbia, S.C., USA; 26 mg, 0.19 mmol), and potassium carbonate (27 mg, 0.19 mmol) in dimethylformamide (2 mL) was heated in the microwave oven at 160 C. for 10 min. Ethyl acetate and water were added, and the aqueous layer was extracted twice with ethyl acetate. The ethyl acetate layers were combined, evaporated, and purified by preparative C18 HPLC, eluting with 10-100% acetonitrile/water. Samples containing the product were extracted twice with dichloromethane and the solvent was evaporated under high vacuum to give 4-[4-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (21 mg, 33%) as a white powder. 1H NMR (300 MHz, DMSO-d6) delta 1.43 (s, 9H), 1.80-2.15 (m, 4H), 3.02 (br s, 2H), 4.08 (d, 2H, J=12.4 Hz), 4.85-5.10 (m, 1H), 6.45-6.52 (m, 1H), 7.58 (d, 1H, J=2.9 Hz), 7.94 (d, 1H, J=2.5 Hz), 8.20 (d, 1H, J=2.5 Hz), 8.22 (s, 1H), 8.50 (s, 1H), 11.85 (br s, 1H). Mass spectrum (ES) MH+=436. HRMS Calcd. for C22H26N7O3 (MH+): 436.2092. Found: 436.2090.

The chemical industry reduces the impact on the environment during synthesis 98549-88-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1990-90-5, name is 3-Methylpyridin-4-amine, the common compound, a new synthetic route is introduced below. COA of Formula: C6H8N2

To a solution of 2-(5-chloro-2-fluorophenyl)-4-iodo-5-methyl-6,7-dihydro-5H-cyclo- pentapyrimidine (275 mg, 0.71 mmol, 1 eq) in dioxane (5 ml) was added Pd(OAc)2 (8 mg, 0.04 mmol, 0.05 eq) followed by BINAP (33 mg, 0.05 mmol, 0.075 eq), 4-amino-3-picoline (84 mg, 0.78 mmol, 1.1 eq) and Cs2CO3 (347 mg, 1.06 mmol, 1.5 eq). The reaction mixture was heated to 80C for 15 h. The reaction mixture was cooled to r.t. and filtered through Celite and the crude material was purified by flash column chromatography (l:l/ethyl acetate:hexane-100% ethyl acetate) to afford [2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-yl]- (3-methyl-pyridin-4-yl)-amine, compound of formula (43) (250 mg, 96%)

The synthetic route of 1990-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 889865-45-6, 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.889865-45-6, name is 2,3-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, molecular weight is 273.89, as common compound, the synthetic route is as follows.

Compound N13z (135 mg, 318 mmol) in 1,4-dioxane (3 mL) was added Pd2(dba)3 (14.5 mg, 0.0159 mmol), XantPhos (18.4 mg, 0.0318 mmol), 2,3-dichloro-4-iodopyridine (109 mg, 0.397 mmol), and DIPEA (0.166 mL, 0.954 mmol). The reaction vessel was purged with argon, sealed, and heated to 110 C. until complete consumption of starting materials. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with water followed by brine. The organic partition was dried over magnesium sulfate, and filtered through Celite. The resulting solution was concentrated and purified by column chromatography (0-100% EtOAc in hexanes). This provided Compound E46a. LCMS ESI+ calc’d for C25H30Cl2N6O2S: 549.2 [M+H+]. found: 549.2 [M+H+].

Statistics shows that 889865-45-6 is playing an increasingly important role. we look forward to future research findings about 2,3-Dichloro-4-iodopyridine.

Reference:
Patent; Gilead Sciences, Inc.; Chin, Gregory; Clarke, Michael O’ Neil Hanrahan; Han, Xiaochun; Hansen, Tim; Hu, Yunfeng Eric; Koltun, Dmitry; McFadden, Ryan; Mish, Michael R.; Parkhill, Eric Q.; Sperandio, David; Xu, Lianhong; Yang, Hai; (199 pag.)US2020/108071; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6000-50-6, 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, 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, Safety of 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, blongs to pyridine-derivatives compound. Safety of 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride

To a solution of 6-(4-aminophenyl)-4-(quinolin-7-yl)pyridazin-3(2H)-one, (800 mg, 2.54 mmol), in tetrahydrofuran, 160 mL, was added 4-nitrophenyl carbonochloridate (615 mg, 3.05 mmol). The reaction mixture was heated at 60 C for 5 hours and concentrated under vacuum. The residue was dissolved in N,N-dimethylformamide, 20 mL and added to 2,3- dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (588 mg, 2.54 mmol) and N,N- diisopropylethylamine, (2.21 mL, 12.7 mmol) in dichloromethane (60 mL) and stirred at r.t. for 16 hours. The precipitate was collected by filtration, washed with water and dried to give the desired product, 850 mg (98% purity, 65% yield over two steps).PRODUCTS: (1029) LC-MS (Method 3): Rt = 0.32 min; MS (ESIpos): m/z = 461 [M+H]+ 1H-NMR (400 MHz, DMSO-D6) delta [ppm]: 4.79-4.81 (m, 4H), 7.41 (d, 1H), 7.54-7.57 (m, 1H), 7.68-7.71 (m, 2H), 7.91-7.93 (m, 2H), 8.03-8.05 (m, 1H), 8.15-8.17 (m, 1H), 8.31 (s, 1H), 8.38-8.40 (m, 1H), 8.46-8.48 (m, 1H), 8.58-8.60 (m, 2H), 8.74 (s, 1H), 8.93-8.94 (m, 1H).

The synthetic route of 6000-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 78607-36-0, 2-Chloro-3-iodopyridine, 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, Computed Properties of C5H3ClIN, blongs to pyridine-derivatives compound. Computed Properties of C5H3ClIN

To a flame-dried flask were added Pd(PPh3)4 (10 mol %), Xantphos (10 mol %), Cs2CO3 (3 eq) and 2-chloro-3-iodopyridine (1.2 eq). Then, 6SB (1 eq) and DMF (0.15 M) were added to the reaction mixture under an N2 atmosphere. The reaction mixture was stirred for 10 min at room temperature, and then heated at 140 C. in a pre-heated oil bath for 24 h. After that, the reaction mixture was cooled to room temperature, diluted with CH2Cl2, filtered through a short pad of Celite, and washed with CH2Cl2. The combined organic extracts were concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to provide the product DFE-6SB-2 in 39% yield.

The synthetic route of 78607-36-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arizona Board of Regents on behalf of Arizona State University; Li, Jian; Zhu, Zhi-Qiang; (232 pag.)US2018/337345; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 89-00-9, name is Pyridine-2,3-dicarboxylic acid, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

A solution of pyridine-2,3-dicarboxylic acid (0.5 g, 3 mmol) and NaOH (0.24 g, 6 mmol) in water (25 mL) was added dropwise with stirring at 60 C to a solution of CdSO4·8/3H2O (0.77 g, 3 mmol) in water (25 mL). A precipitate immediately formed and stirring was continued for 4 h at 50 C. The addition of the 2-meim ligand (0.49 g, 6 mmol) in water (10 mL) to the precipitate mixture resulted in a clear solution. The mixture was stirred for 2 h at 60 C and then cooled to room temperature. The crystals that formed were filtered, washed with 10 mL of water, and dried in air. The crystals were collected for 1 in 69.3% yield. Anal. Calc. for C11H9CdN3O4: C, 36.74; H, 2.52; N, 11.68. Found: C, 36.67; H, 2.71; N, 11.52%.

The synthetic route of 89-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Semerci, Fatih; Ye?ilel, Okan Zafer; Soylu, Mustafa Serkan; Keskin, Seda; Bueyuekguengoer, Orhan; Polyhedron; vol. 50; 1; (2013); p. 314 – 320;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.105596-61-0, name is Ethyl 2-methoxyisonicotinate, molecular formula is C9H11NO3, molecular weight is 181.19, as common compound, the synthetic route is as follows.Recommanded Product: Ethyl 2-methoxyisonicotinate

A solution of ethyl 2-methoxy-pyridine-4-carboxylate (0.93 g, 5 mmol) in ether (5 ml) was added to lithium aluminium hydride (0.3 g, 8 mmol) in ether (10 ml) cooled to 5 C. and the mixture stirred for 2 hours. Water was added, the mixture was filtered through diatomaceous earth and the pad was washed through with ethyl acetate. The filtrate was extracted with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 4-hydroxymethyl-2-methoxypyridine (0.64 g, 89%) as a yellow oil. 1 H NMR Spectrum: (CDCl3) 3.86(s, 3H); 4.62(s, 2H); 6.65(s, 1H); 6.76(d, 1H); 8.05(d, 1H) MS – ESI: 140 [MH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105596-61-0, Ethyl 2-methoxyisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
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. 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4,6-Dichloronicotinic acid

The solution of Example 146a (3.0 g, 19.2 mmol, 1.0 eq) in POCl3(30 mL) was stirred for 4 h at 100oC. After the reaction completed, it was concentrated under vacuo to give crude product (3.0 g, crude) which was used to next step without further purification.

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, 73027-79-9, 4,6-Dichloronicotinic acid.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; KALDOR, Stephen W.; (0 pag.)WO2020/86616; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem