Tag: M.W:200-300

Related Products of 230301-11-8 , The common heterocyclic compound, 230301-11-8, name is tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, molecular formula is C11H17N3O2, 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.

A solution of 6-chloro-N-[4-ethyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl]pyrimidin-4-amine (150 mg, 472 muetaiotaomicron) and tert-butyl 1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate (158 mg, 708 muiotaetaomicron, CAS 230301-11-8) in DMF (2.5 mL) was treated with caesium carbonate (461 mg, 1.42 mmol). The reaction mixture was stirred at 120C overnight and an additional night at 140C. The mixture was diluted with water, three times extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by preparative reverse phase HPLC (method: column: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / eluent: A = water (0,01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10% B, 6.50 min = 20% B, 17.0-19.75 min = 100% B, 19.75-23.00 min = 90% B). Subsequently the obtained regioisomeric mixture was separated using (HPLC) method to yield 13.2 mg (6% yield) of the desired product. LC-MS (method 9): Rt = 1.18 min; MS (ESIpos): m/z = 505 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm] : -0.008 (3.40), 0.008 (2.05), 0.988 (1.10), 1.007 (2.36), 1.025 (1.06), 1.073 (0.74), 1.091 (1.48), 1.108 (0.71), 1.424 (16.00), 2.328 (0.41), 2.519 (2.00), 2.524 (1.93), 3.214 (0.83), 3.375 (0.71), 3.392 (0.70), 3.593 (0.62), 3.607 (1.06), 3.621 (0.50), 4.382 (1.39), 7.339 (0.53), 7.361 (1.03), 7.383 (0.62), 7.586 (0.61), 7.600 (0.70), 7.622 (0.53), 7.661 (1.24), 8.459 (0.81), 9.416 (0.72), 12.813 (0.67).

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; KLAR, Juergen; EHRMANN, Alexander; WILLWACHER, Jens; ENGEL, David; DIESKAU, Andre Philippe; KAHNERT, Antje; GROMOV, Alexey; SCHMECK, Carsten; LINDNER, Niels; MUeLLER, Thomas; ANDREEVSKI, Anna Lena; DREHER, Jan; COLLINS, Karl; (861 pag.)WO2018/69222; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1214334-70-9, 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. A new synthetic method of this compound is introduced below.

[0436] To a stirred solution of 5-bromo-6-methoxypicolinic acid (350 mg, 1 mmol) in CH2C12 (2 mL) under an argon atmosphere were added oxalyl chloride (347 mg, 2 mmol) and DMF (catalytic amount) at 0 C. The reaction mixture was stirred at room temperature for 2 h. After consumption of acid (by TLC), the volatiles were evaporated in vacuo to give 5- bromo-6-methoxypicolinoyl chloride.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214334-70-9, 5-Bromo-6-methoxypicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 175205-82-0, 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 175205-82-0 as follows.

2-Bromo-3-(trifluoromethyl)pyridine (1 .5 g, 6.63 mmol) is added to a solution of example 16a (500 mg, 2.21 mmol) in TEA (3.5 mL, 25.25 mmol) and dry ACN (14 mL) at rt. Then Copper (I) Iodide (84 mg, 0.442 mmol) and dichlorobis(triphenylphosphine)palladium(II) (155 mg, 0.221 mmol) are added and stirring is continued overnight. Solvent is evaporated under reduced pressure and the crude is purified byflash chromatography (eluent 0-40% EtOAc/cyclohexane) to furnish the title compound (800 mg, 99%).U PLC-MS (Method 2): R = 1 .23 mm MS (ESI pos): mlz = 363 (M+H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175205-82-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; CUI, Yunhai; DOODS, Henri; FERRARA, Marco; JUST, Stefan; KUELZER, Raimund; LINGARD, Iain; MAZZAFERRO, Rocco; RUDOLF, Klaus; WO2014/184275; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 160599-70-2, 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. 160599-70-2, name is 2,5-Dibromo-3-chloropyridine, molecular formula is C5H2Br2ClN, 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.

A 100-mL pressure vessel was charged with 4,4,5, 5-tetramethyl-2-(4- (phenylsulfonyl)phenyl)-l,3,2-dioxaborolane (6.34 g, 18.43 mmol), 2,5-dibromo- 3-chloropyridine (5.00 g, 18.43 mmol, Sigma-Aldrich, St. Louis, MO), potassium carbonate (7.64 g, 55.3 mmol), tetrakis(triphenylphosphine)palladium (1.06 g, 0.92 mmol, Strem Chemical Inc, Newburyport, MA), 20 mL of 1,2- dimethoxy ethane, and 4 mL of water. The vessel was sealed and the reaction mixture was heated at 100 C for 8 h. After cooling to room temperature, the mixture was diluted with EtOAc (30 mL) and water. The layers were separated and the organic phase was dried (MgS04), filtered, and concentrated under a vacuum to give an oil. Purification via column chromatography (40 g of silica gel, 0 to 50% EtOAc in hexanes) produced 5-bromo-3-chloro-2-(4- (phenylsulfonyl)phenyl)pyridine (2.56 g) as a tan solid.

According to the analysis of related databases, 160599-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); 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. 72830-09-2, name is 2-Chloromethyl-3,4-dimethoxypyridinium chloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Chloromethyl-3,4-dimethoxypyridinium chloride

10% NaOH solution (42.5 gm in 425 ml of water) is added drop wise to a solution of 5-(difluoromethoxy)-2-mercapto benzimidazole (100.0 gm; 0.462 moles) in methanol(350.0 ml) at 10-150C. To the above solution a clear solution of 2-chloro-3, 4-dimethoxy pyridine hydrochloride (105.5 gm.0.473 moles in 525 ml of methanol) was added at 10-150C. The reaction mass was maintained at 10-15C for 30 minutes. The temperature of the reaction mass was slowly raised to 2O0C. The reaction mass was maintained at 20-25 C for 2 hours. Further the temperature was raised to 400C and maintained at 400C. Completion of the reaction is monitored by TLC. After completion of the reaction methanol is evaporated under reduced pressure to get a residue. Chilled water (600 ml) was added to the residue and the reaction mass was extracted with methylene chloride (600 ml, 300 ml x 2). The organic layers were separated and evaporated under reduced pressure to obtain a residue. Isopropyl alcohol (50 ml) and hexane (600 ml) were added to the reaction mass. The reaction mass was cooled to 0-50C and maintained at 0-5C for 30 minutes. The reaction mass was filtered at 0-5C and washed with chilled hexane (100 ml). The solids were dried under vacuum at 4O0C; Dry wt-162 gm (Yield=95.3%); HPLC Purity=99.21% w/w.; Melting range=l 15-1170C (Lit.7mp-H5-1 18C); MS (ESI); 368.0(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, 72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride.

Reference:
Patent; MACLEODS PHARMACEUTICALS LIMITED; WO2009/66317; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 83004-10-8, 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.83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

To a solution of 0.855 ml of diisopropylamine in 15 ml of tetrahydrofuran was added 2.26 ml of a hexane solution containing 2.66 M n-butyllithium at O0C, followed by stirring the reaction mixture at 00C for 30 minutes. After cooling down to -78C, a solution of 1.54 g of 1- tert-butyl 4-ethyl piperidine-l,4-dicarboxylate in 5 ml of tetrahydrofuran was added to the reaction mixture, and the resultant mixture was stirred at -78C for 30 minutes. A solution of 1.00 g of 2-bromo-6-(bromomethyl)pyridine in 5 ml of tetrahydrofuran was added to the reaction mixture, followed by stirring the reaction mixture at -78C for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extracting with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate = 20/1 – 2/1) to give the title compound as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis 83004-10-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; WO2009/104802; (2009); 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. 89466-18-2, name is 6-Bromo-2-methoxypyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-Bromo-2-methoxypyridin-3-amine

At room temperature, 6-bromo-2-methoxypyridin-3-amine (12.00 g, 59.10 mmol),Acetic anhydride (48.67 g, 466.90 mmol) was terminated at 20 C for 1 h. The reaction solution was added with water (240 ml) and stirred for 1 h. A brown precipitate was precipitated, filtered with suction, and the filter cake was dried.The yield was 9.80 g of brown solid with a yield of 68%.

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, 89466-18-2, 6-Bromo-2-methoxypyridin-3-amine.

Reference:
Patent; Jiangsu Weikaier Pharmaceutical Technology Co., Ltd.; Gong Yanchun; Meng Lei; Guo Qirun; Liu Yongqiang; (65 pag.)CN110642838; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 796851-03-1, 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. 796851-03-1, name is 2,5-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, 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.

a) A mixture of 2,5-dichloro-4-iodopyridine (0.56 g, 2.04 mmol), 2-amino-N-methyl- 5-(4-methylpiperazin-l-yl)benzamide (0.508 g, 2.04 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (0.071 g, 0.12 mmol), cesium carbonate (1.332 g, 4.09 mmol) and palladium(II) acetate (0.018 g, 0.08 mmol) was suspended in DMA (15 mL). The mixture was heated at 1000C for 1 hour in a microwave reactor and then allowed to cool to room temperature. The mixture was loaded onto an SCX column and the product eluted first using MeOH and then with a 7M solution of NH3 in MeOH. Fractions containing product were combined and evaporated to afford 2-[(2,5-dichloropyridin-4- yl)amino]-N-methyl-5-(4-methylpiperazin-l-yl)benzamide as a DMA adduct (0.990 g); 1H NMR spectrum: (300 MHz, DMSO) delta 2.23 (3H, s), 2.44 – 2.50 (4H, m), 2.73 (3H, d), 3.16 – 3.21 (4H, m), 6.90 (IH, s), 7.10 – 7.14 (IH, m), 7.20 (IH, d), 7.40 (IH, d), 8.19 (IH, s), 8.58 (IH, d), 9.67 (IH, s); Mass spectrum: m/z (ESI+) (M+H)+ = 394.09.

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 796851-03-1, 2,5-Dichloro-4-iodopyridine.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/153589; (2009); 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 62774-90-7, name is 2,6-Dichloro-4-methylnicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H5Cl2NO2

tert-Butyl 2, 6-dichloro-4-methylnicotinate: To a solution of 2,6-dichloro-4-methylnicotinic acid (1.00 g, 4.85 mmol, 1 equiv) in tert-butyl acetate (24 mL) wasadded 70% perchioric acid (0.88 mL, 14.56 mmol, 3 equiv). After 1 h, reaction was diluted with DCM, washed cautiously with saturated aqueous sodium bicarbonate solution, dried (Na2SO4), and concentrated in vacuo to provide the product (1.21 g, 95%) as a pale yellow oil.1H NMR (400 MHz, CDC13) oe 7.15 (s, 1H), 2.37 (d, J0.5 Hz, 3H), 1.62 (s, 9H); LCMS (ESI, M+1): 262.1.

With the rapid development of chemical substances, we look forward to future research findings about 62774-90-7.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; CONNOLLY, Timothy P.; EASTMAN, Kyle J.; (60 pag.)WO2016/33009; (2016); 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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H4BrClN2

5-Bromo-2-chloro-3-pyridinamine (10 g) was dissolved in pyridine (75 ml) and methanesulfonyl chloride (7.5 ml) was added and stirred overnight. Further methanesulfonyl chloride (2.1 ml) was added and the reaction stirred at RT for 5 h. Further methanesulfonyl chloride (2.1 ml) was added and the mixture stired at RT overnight. The ph was adjusted to -6 by addition of 2M HCI (aq). The mixture was extracted with DCM (2 x 150 ml) and the combined organic layers were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was suspended in methanol (200 ml) and 2M NaOH (50 ml) was added. The mixture was stirred for 1 h and then the solvent removed in vacuo. The residue was dissolved in water (250 ml) and washed with DCM (150 ml). The aqueous layer was acidified and the resulting precipitate collected by filtration. The solid was air dried overnight to give the title compound as an off white solid, 13.45 g.LCMS (method B); Rt = 0.81 min, MH” = 285.

The synthetic route of 588729-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian Robert; DOWN, Kenneth David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie Nicole; JONES, Katherine Louise; JONES, Paul Spencer; LE, Joelle; LUNNISS, Christopher James; PARR, Nigel James; RITCHIE, Timothy John; ROBINSON, John Edward; SIMPSON, Juliet Kay; SMETHURST, Christian Alan Paul; WO2011/67365; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem