Day: April 18, 2022

Application of 185315-53-1 ,Some common heterocyclic compound, 185315-53-1, molecular formula is C6H5Cl2N, 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.

General procedure: A mixture of N-tert-butyl-7-(3,3-difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5- amine (25 mg, 0.08 mmol), NEt3 (14.6 mg, 0.144 mmol) and l-(bromomethyl)-2- (trifluoromethyl)benzene (26.8 mg, 0.112 mmol) in 2 mL DMF was stirred at room temperature for 5 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt . After evaporation of the product containing fractions 5.2 mg (14 %) of the title compound was isolated. MS(m/e): 456.4 (MH+). Example 24; N-tert-Butyl-3-[(3-chloropyridin-2-yl)methyl]-7-(3,3-difluoropyrrolidin-l-yl)triazolo [4,5-d]pyrimidin-5-amine; In analogy to the procedure described for the synthesis of N-tert-butyl-7-(3,3- difluoropyrrolidin- l-yl)-3-[[2- (trifluoromethyl)phenyl] methyl] triazolo [4, 5 -d] pyrimidin- 5 – amine (example 22) the title compound was prepared from N-tert-butyl-7-(3,3- difluoropyrrolidin-l-yl)-3H-triazolo[4,5-d]pyrimidin-5-amine and 3-chloro-2- (chloromethyl)pyridine. MS(m/e): 423.3 (MH+).

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. 185315-53-1, 3-Chloro-2-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ROEVER, Stephan; ROGERS-EVANS, Mark; NETTEKOVEN, Matthias; SCHMITT, Sebastien; GRETHER, Uwe; KIMBARA, Atsushi; WO2015/32769; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145255-19-2, 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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide. A new synthetic method of this compound is introduced below.

To a flask charged with 5-aminopyridine-2-carboxamide (48 mg, 0.35 mmol) and DIEA (0.150 mL, 0.861 mmol) in dichloromethane (1 mL) was added a solution of 4-(difluoromethoxy)-2- fluoro-6-[2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy]benzoyl chloride ( 100 mg, 0.231 mmol) in dichloromethane ( 1.5 mL) at 0 C dropwise under an N2 atmosphere. The reaction mixture was stirred for 16 hours at room temperature then diluted with water and extracted with dichloromethane. The organic layer was dried over MgSO/t, filtered and concentrated in vacuo. Silica gel chromatography (0-60% ethyl acetate/hexanes) provided 5-[[4-(difluoromethoxy)-2-fluoro-6-[2-(trideuteriomethoxy)-4- (trifluoromethoxy)phenoxy]benzoyl]amino]pyridine-2-carboxamide (22 mg, 18%). ESI-MS m/z calc. 534.10, found 535.2 (M+l)+; retention time (Method B): 1.67 minutes (3 minute run). ‘H NMR (400 MHz, DMSO-d6) 5 11.18 (s, 1H), 8.85 (dd, J = 2.5, 0.7 Hz, 1H), 8.25 (dd, J = 8.6, 2.5 Hz, 1H), 8.08 – 7.97 (m, 2H), 7.60 – 6.93 (m, 6H), 6.37 (t, J = 1.7 Hz, 1H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,145255-19-2, 5-Aminopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66909-38-4, 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.66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

2-Chloro-4-methyl-5-nitropyridine (lg, 5.8 mmol) was dissolved in EtOH (60 mL). AcOH (4 mL) and Fe (5 eq. ) were added and the mixture was refluxed at 80C overnight. The mixture was filtered through celite and reduced under vacuum to afford the crude 5-amino-2-chloro-4-methylpyridine which was used in the next step with no further purification. The amine was dissolved in cone. HC1 (6 mL), transferred to a 3-neck round bottom flask, and cooled to-5 C. A solution of NaNO2/H2O (440 mgs/5 mL) was slowly added and the mixture was allowed to stir for 10 mins. To a second, separate 3-neck round bottom flask was added H20 (12 mL) and cooled to-5 C. Thionyl chloride (4.5 eq. ) was then added dropwise. After complete addition the mixture was allowed to warm to room temp. Whereupon CuCl (. 05 eq. ) was added and the mixture was then cooled back down to -5C. The first reaction mixture, containing the amine precursor, was slowly added to the second reaction mixture. A froth formed and was filtered off to afford 6-chloro-4-methyl-pyridine-3-sulfonyl chloride which was used in the next step with no further purification. The title compound was synthesized from 2- [2- (R, S)-3-oxo-1, 2,3, 4-tetrahydro-quinoxalin-2-yl]-N- (pyrid- 4-yl) ethyl acetamide and 6-chloro-4-methyl-pyridine-3-sulfonyl chloride using Method G. MS ni/z (M+H) 501.4 ; HPLC (CH3CN-H2O-0.1% TFA): Rt= 2.05 min.

Statistics shows that 66909-38-4 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/93245; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 936011-17-5, 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 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of compound 39-1 (30 g, 139 mmol) and Et3N (27 g, 280 mmol) in 100 mL ofmethanol was added Pd(dppf)Ch (10.5 g, 139 mmol). The resulting mixture was stirred underCO (50 Psi) at 70 oc for 12 hours. After cooling, filtration and concentration, the resultingresidue was purified by column chromatography on silica gel (eluted with petroleum ether_ethylacetate= 3:1) to give 39-2. MS(ESI) m/e (M+H+): 196.0.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; NARGUND, Ravi P.; BLIZZARD, Timothy A.; JOSIEN, Hubert; BIJU, Purakkattle; PLUMMER, Christopher W.; DANG, Qun; LI, Bing; LIN, Linus S.; CUI, Mingxiang; HU, Bin; HAO, Jinlai; CHEN, Zhengxia; WO2014/19186; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 204378-41-6, Methyl 6-chloro-4-methoxypicolinate, 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

(2) Synthesis of 6-chloro-4-methoxypicolinic Acid [Compound (II-75)] Using 6-chloro-4-methoxypicolinic acid methyl ester [Compound (V-75)] (0.5 g, 2.48 mmol), the Compound (II-75) was synthesised according to the process of Synthesis Example 20 (3). White solid, yield: 0.45 g, percent yield: 97.0percent, m.p.: 183-185° C. IR KBr cm-1: 1707, 1599, 1473, 1320, 1284, 1107, 1038, 921, 870, 723. 1H-NMR (60 MHz, d6-DMSO, delta): 3.84 (3H, s, OCH3), 6.94 (1H, d, J=2 Hz, pyridine ring H), 7.45 (1H, d, J=2 Hz, pyridine ring H), COOH indistinctness.

The synthetic route of 204378-41-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kureha Kagaku Kogyo K.K.; US6610853; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 109613-97-0, 2-Bromo-4-methoxypyridin-3-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, 109613-97-0, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-4-methoxypyridin-3-amine

To a solution of 2-bromo-4-methoxypyridin-3-amine (2.1 g, 10.34 mmol), N-(4-ethynylpyridin-2-yl)acetamide (1.82 g, 11.38 mmol) in DMF (15 mL) was added TEA (21.62 mL, 155 mmol) and CuI (0.12 g, 0.62 mmol). The reaction mixture was purged with nitrogen for 2 min, followed by addition of Pd(PPh3)2Cl2 (0.73 g, 1.03 mmol). The reaction mixture was then heated at 100 C. for 3 h. The reaction mixture was cooled down and diluted with ethyl acetate and saturated NaHCO3 solution. The organic layer (two times extracts) were combined, washed with saturated NaHCO3 solution, dried over MgSO4. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography. The product was eluted with DCM to 50% of 10% MeOH in DCM to give the desired product as a light yellow (1.0 g, 34%); HPLC: RT=0.48 min (H2O/ACN with 0.05% TFA, Waters Acquity SDS C18, 2.1×50 mm, 1.7-mum particles, gradient=1.8 min, wavelength=220 nm); MS (ES): m/z=283.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) delta ppm 10.59 (s, 1H), 8.34 (dd, J=5.1, 0.7 Hz, 1H), 8.22 (s, 1H), 7.79 (d, J=5.3 Hz, 1H), 7.34 (dd, J=5.2, 1.4 Hz, 1H), 6.91 (d, J=5.3 Hz, 1H), 5.35 (s, 2H), 4.03 (q, J=7.2 Hz, 1H), 3.88 (s, 3H), 2.11 (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,109613-97-0, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; Fink, Brian E.; Zhao, Yufen; Borzilleri, Robert M.; Zhang, Liping; Kim, Kyoung S.; Kamau, Muthoni G.; Tebben, Andrew J.; (162 pag.)US2016/176871; (2016); A1;,
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.116026-95-0, name is tert-Butyl (4-formylpyridin-3-yl)carbamate, molecular formula is C11H14N2O3, molecular weight is 222.24, as common compound, the synthetic route is as follows.Computed Properties of C11H14N2O3

Step 2, Method 8: tert-But l iV-[4-(6-Methoxy-l,3-benzothiazol-2-yl)pyridin-3- yl] carbamate[0172] To a stirred solution of 2-[(2-amino-5-methoxyphenyl)disulfonyl]-4- methoxyaniline (100 mg, 0.324 mmol) and te^butyl(4-formylpyridin-3-yl)carbamate (144 mg, 0.648 mmol) in N,N-dimethylformamide (3 mL) under nitrogen was added sodium metabisulfite (123 mg, 0.648 mmol). The reaction mixture was heated to 130 C and stirred for 1.5 hours. The mixture was allowed to cool to room temperature then ethyl acetate (10 mL) and water (10 mL) added and thelayers separated. The organic layer was washed with water (2 x 10 mL) and brine (2 x 10 mL). The combined organic layers were dried over magnesium sulphate, concentrated, recrystallised twice from methanol (8 mL) and the resulting solid dried under suction to give the title compound 50 mg (21% yield) as an off-white powder. 5H NMR (500 MHz, DMSO) 10.76 (s, 1H), 9.32 (s, 1H), 8.43 (d, J = 5.1 Hz, 1H), 7.98 (d, J = 9.0 Hz, 1H), 7.89 (d, J = 5.1 Hz, 1H), 7.82 (d, J = 2.5 Hz, 1H), 7.22 (dd, J = 9.0, 2.5 Hz, 1H), 3.88 (s, 3H), 1.49 (s, 9H). Tr(MET-uHPLC-AB-lOl) = 4.1 min, (ES+) (M+H)+358.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116026-95-0, tert-Butyl (4-formylpyridin-3-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; BROWN, Christopher, John; PRIME, Michael, Edward; WEDDELL, Derek, Alexander; WALTER, Daryl, Simon; GILES, Paul, Richard; WIGGINTON, Ian, James; TAYLOR, Malcolm, George; GALAN, Sebastien, Rene, Gabriel; JOHNSON, Peter, David; KRUeLLE, Thomas, Martin; MORAO, Inaki; CLARK-FREW, Daniel; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; (120 pag.)WO2016/33460; (2016); 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below., SDS of cas: 709652-82-4

Boronate 10: Compound 9 (50 g, 0.224 mol), bis(pinacolato)diboron (85.6 g, 0.337 mol), KOAc (44.1 g, 0.449 mol) and Pd(dppf)Cl2.CH2Cl2 (2.77 g, 3.4 mmol) were charged into a flask. Dioxane (400 mL) was added. The reaction mixture was stirred at 100 C. for 2 hr under Ar. When LC-MS indicated that the reaction was completed, the mixture was cooled to room temperature. The mixture was filtered through diatomite, concentrated, diluted with a mixture of ethyl acetate and hexane in 3/1 ratio (1000 mL), filtered through silica gel (300-400 mesh), concentrated, crystallized and dried to give boronate 10 (32 g, 66%) as a white solid.

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, 709652-82-4, 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; ABUDUSAIMI, Mamuti; YE, Fangguo; SUN, Jiangqin; MIYAMOTO, Hisashi; CHENG, Jay-Fei; OKA, Daisuke; US2014/179675; (2014); 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 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.

With the rapid development of chemical substances, we look forward to future research findings about 1149-24-2.

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

Electric Literature of 884494-52-4, 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. 884494-52-4, name is 3-Bromo-2-fluoro-4-iodopyridine. A new synthetic method of this compound is introduced below.

In a dry 3 neck 2 L flask equipped with a dry addition funnel, thermometer and stir bar was added 3- bromo-2-fluoro-4-iodopyridine (83.4 g, 276 mmol) followed by 300 mL of anhydrous THF under an atmosphere of nitrogen. The solution was cooled to -7O0C in 2-propanol/dry ice bath. A solution of isopropylmagnesium chloride 2.0 M in diethyl ether (145 mL, 290 mmol) was added drop wise over a period of 30 minutes. The solution was then stirred for 30 minutes before zinc (II) chloride 0.5 M in THF (276 mL, 138 mmol) was cannulated in. The solution was warmed to room temperature and stirred for lhour. The addition funnel was replaced with a reflux condenser and N4-cyclopentyl-5-iodopyrimidine-2,4-diamine (243, see example 200) (28.00 g, 92.1 mmol) was added, followed by Pd(PPh3)4 (5.32 g, 4.60 mmol). The solution was heated over night at a gentle reflux. After concentrating the solution to 1/1 Oth of the volume under vacuum, it was cooled in an ice bath. To this was added 100 mL of cold saturated NH4Cl, followed by 500 mL of water. 50OmL of 12% isopropanol/DCM was then added and the solution was stirred at room temperature for lhour before being filtered through filter paper. The filter cake was washed in succession with water, DCM and 12% 2-propanol /DCM. The filtrate was partitioned in a separation runnel and the aqueous layer was washed with 12% 2-propanol /DCM. The organics were dried over MgSO4 and then concentrated under vacuum. The residue obtained was partially dissolved in DCM with sonication and filtered off to give compound 244 (26.45g, 81.6%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta ppm 8.18 (1 H, d, J= 4.9 Hz), 7.52 (1 H, s), 7.26 (1 H, dd, J= 4.9, 0.7 Hz), 6.34 (2 H, s), 6.12 (1 H, d, J= 7.6 Hz), 4.42 (1 H, sxt, J= 7.4 Hz), 1.76 – 1.96 (2 H, m), 1.55 – 1.68 (2 H, m), 1.31 – 1.53 (4 H, m) ) ppm; LCMS-ESI (POS), M/Z, M+l : Found 352.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-52-4, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/85185; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem