Tag: M.W:100-200

Synthetic Route of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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.

NaH (570 mg, 14.24 mmol) was added portion wise to stirred anhydrous DMSO (10 ml_). The mixture was heated to 80C until evolution of gas ceased and then cooled to 0C. A solution of (carbethoxymethyl)- triphenylphosphonium bromide (3.05 g, 7.12 mmol) in DMSO (10 ml_) was then added and the mixture stirred at r.t for 30 min. The mixture was cooled to 0C and a solution of 5-chloronicotinaldehyde (1 .0 g, 7.12 mmol) in DMSO (10 ml_) was added and the mixture was stirred at r.t for 1 h. The mixture was then poured into aqueous 1 M HCI and extracted into DCM (3 x 50 ml_). The organics were combined and washed with H2O (3 x 100 ml_) and brine (3 x 100 ml_), separated, dried (MgSO ) and concentrated. Purification by flash silica column chromatography (gradient elution /’-hex to 25% EtOAc in /-hex) gave the title compound as a yellow solid (1 .1 g, 57%). LCMS (ES+) 271 (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,113118-82-4, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; LUCKHURST, Christopher A.; HAUGHAN, Alan F.; BRECCIA, Perla; STOTT, Andrew J.; BURLI, Roland W.; HUGHES, Samantha J.; MUNOZ-SANJUAN, Ignacio; DOMINGUEZ, Celia; MANGETTE, John E.; WO2012/103008; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, 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. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, 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.

Example 12N-[6-(1 H-lndol-4-yl)-1 H-indazol-4-yl]pyrazolo[1 ,5-a]pyridine-2-carboxamide Pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (27 mg, 0.166 mmol) was treated with anhydrous THF (2ml) and then 1-chloro-N, N, 2-trimethylpropenylamine (0.026 ml, 0.20 mmol). The reaction was stirred at room temperature under nitrogen for 2 hrs. The reaction was then treated with anhydrous DIPEA (0.131 ml, 0.753 mmol) and 2ml of solution of 6-(1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (750mg, 2.26 mmol) in THF (30ml). The reaction was then stirred at room temperature under nitrogen for 69 hrs. The solvent was blown -off under a stream of nitrogen, dissolved in methanol (3ml) and then solvent removed under reduced pressure. The crude reaction mixture was dissolved in methanol (5ml), treated with Macroporous Tosic Acid (4.45 mmol/g, 102 mg, 0.45 mmol), stirred at room temperature for 17 hrs and then treated with 0.88 ammonia (0.5 ml), stirred for 30 minutes and then filtered. The solvent was removed under reduced pressure and then the residue purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound. LCMS (Method B) m/z 393 [MH+], R1 = 1.02min.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147189; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 697739-12-1, 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.697739-12-1, name is Ethyl imidazo[1,5-a]pyridine-8-carboxylate, molecular formula is C10H10N2O2, molecular weight is 190.2, as common compound, the synthetic route is as follows.

Ethyl imidazo [1, 5-a] pyridine-8-carboxylate (J. Het. CLIEIIZ., 1993,473) (0.21 g) was dissolved in 1M KOH in methanol (5 ml) and the solution heated at reflux for 5 min. The mixture was then concentrated, diluted with water (2 ml) and acidified to pH 1 with 2N HCI. The resulting precipitate was collected by filtration to give imidazo [1, 5-a] pyridine-8-carboxylic acid (80 mg) as a yellow solid.

Statistics shows that 697739-12-1 is playing an increasingly important role. we look forward to future research findings about Ethyl imidazo[1,5-a]pyridine-8-carboxylate.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/28445; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1849-52-1, 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 1849-52-1, name is 3-Methoxyisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Compound VI (23.8 g, 0.1 mol) was added to a 500 mL three-necked flask. Add tetrahydrofuran (100 mL), The stirring was started, and tetramethylpiperidine lithium (LTMP) (44 mL, 0.11 mol) was added dropwise at -40 ° C under nitrogen atmosphere. After the addition is completed, continue to stir for 0.5 hours. Then, a solution of 3-methoxy-4-pyridinecarboxaldehyde (13.7 g, 0.1 mol) in tetrahydrofuran was added dropwise. After the drop, continue to react at -40 ° C for 1 hour, TLC point plate monitoring,After the material point disappears, a saturated ammonium chloride solution is added dropwise below zero, and ethyl acetate is added. Extract, separate the organic layer, add anhydrous sodium sulfate to dry, filter,The filtrate was concentrated under reduced pressure.Obtained a yellow solid compound V-1, 32.9 g,The yield was 88percent.

According to the analysis of related databases, 1849-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Jin Yanjuan; (11 pag.)CN108689998; (2018); 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. 1032943-43-3, name is 4-Bromo-1H-pyrazolo[3,4-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Bromo-1H-pyrazolo[3,4-c]pyridine

4-Bromo- lH-pyrazolo[3 ,4-c]pyridine (2 g, 10.10 mmol) was dissolved in DCM (30 niL) and m-CPBA (2.61 g, 15.15 mmol) was added at 0 C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, solid precipitate was filtered and dried to afford 4-bromo-6-oxido-lH-pyrazolo[3,4-c]pyridin-6-ium (I, 2 g, 9.34 mmol, 92 52% yield). LCMS (ES +): m/z 215 [M + l l j

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, 1032943-43-3, 4-Bromo-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; HENDERSON, James, A.; VORA, Harit, U.; VEITS, Gesine, Kerstin; PHILIPS, Andrew, J.; (576 pag.)WO2020/51235; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 136888-17-0 ,Some common heterocyclic compound, 136888-17-0, molecular formula is C7H5ClN2O, 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 mixture of 5-chloro-l /-pyrrolo[2,3-c]pyridin-2(3 /)-onc (Step 3 of Intermediate B7) (750 mg, 4.44 mmol) and triethyl orthoacetate (10 mL) was heated at 130 C for 1 h. The reaction mixture was concentrated under reduced pressure and the solid was stirred with diethyl ether. The compound was filtered and dried to yield 800 mg of the desired compound. NMR (400 MHz, DMSO-de) d 1.44 (t, J= 7.2 Hz, 3H), 2.78 (s, 3H), 4.45 (q, J= 7.2 Hz, 2H), 7.41 (s, 1H), 7.82 (s, 1H), 10.58 (s, 1H).

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. 136888-17-0, 5-Chloro-1H-pyrrolo[2,3-c]pyridin-2(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ICHNOS SCIENCES S.A.; CHAUDHARI, Sachin, Sundarlal; GHARAT, Laxmikant, Atmaram; IYER, Pravin; DHONE, Sachin, Vasantrao; ADIK, Bharat, Gangadhar; WADEKAR, Prashant, Dilip; GOWDA, Nagaraj; BAJPAI, Malini; (233 pag.)WO2020/70331; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6515-09-9, 2,3,6-Trichloropyridine, 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, 6515-09-9, blongs to pyridine-derivatives compound. Computed Properties of C5H2Cl3N

A solution of n-butyllithium in hexanes (2.5M, 30 mmol, 12 mL) was added drop-wise to a solution of (1321) diisopropylamine (30 mmol, 4.3 mL) in dry THF (100 mL) at -78 C. After 1 hour, a solution of 2,3,6- trichloropyridine (27.4 mmol, 5 g) in dry THF (25 mL) was added over 15 minutes. After a further 1 hour, a (1322) solution of methyl iodide (30.4 mmol, 1.9 mL) in dry THF (10 mL) was added drop-wise over 5 minutes. The orange- brown solution was stirred at -78 C for 15 minutes, then allowed to warm to room temperature and stirred at room temperature for 18 hours. The reaction was carefully quenched by the addition of saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried (MgS04) and concentrated under reduced pressure. Partial purification of the crude product was achieved by column chromatography (silica gel, gradient of ethyl acetate in isohexane) to give the intermediate 2 , 3 , 6-trichloro-4-methylpyridine as an oily colourless solid (2.4 g) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6515-09-9, its application will become more common.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63572-73-6, Adding some certain compound to certain chemical reactions, such as: 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine,molecular formula is C6H4N4O2, 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 63572-73-6.

Compound 1 (2 g, 12.2 mmol, 1.0 eq),Soluble in DMF (20mL),NBS (2.5 g, 14.0 mmol, 1.15 eq) was added in portions at 0 C.The reaction was carried out for 16 hours at room temperature.LCMS showed the reaction of the starting material,There is product generation. Concentrate and spin dry to a crude product.Purified by column (PE/EA=100:1-10:1),Yellow solid compound 2 (1.4 g, yield: 94%).

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. 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Kefeipingshenghui Pharmaceutical Co., Ltd.; Jin Qiu; Qin Yinlin; Su Mei; Qiu Yanan; Lou Yajing; (23 pag.)CN109206401; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route 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.

B) 5-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)pyridine-2-carboxamide To a solution of (3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile (200 mg) obtained in Step A of Example 8, 5-aminopyridine-2-carboxamide (130 mg) obtained in Step A of Example 350, cesium carbonate (520 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (75 mg) in tetrahydrofuran (5.0 mL) was added tris(dibenzylideneacetone)dipalladium(0) (73 mg), and the mixture was stirred overnight at 80C under argon atmosphere. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized (diisopropyl ether/ethanol) to give the title compound (25 mg). MS (ESI+) : [M+H]+ 352.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145255-19-2, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TSUKAMOTO, Tetsuya; OHBA, Yusuke; YUKAWA, Takafumi; NAGAMIYA, Hiroyuki; KAMEI, Taku; TOKUNAGA, Norihito; SAITOH, Morihisa; OKABE, Atsutoshi; EP2832734; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41288-96-4, 2-Chloro-5-hydroxypyridine, 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, Formula: C5H4ClNO, blongs to pyridine-derivatives compound. Formula: C5H4ClNO

General procedure: To a vigorously stirred solution of 2-chloro-6-hydroxypyridine(0.13 g, 1.0 mmol) in acetonitrile (2 mL) at room temperature was added a 6 M aqueous solution of potassium hydroxide (2 mL). Difluoromethyltriflate (0.38 mL, 3.0 mmol, 3 equiv.) was added dropwiseto the reaction mixture which was maintained at room temperature by means of a water bath (the reaction is exothermic), and the medium was stirred for 30 min. The mixture was diluted with water(20 mL) and extracted with diethyl ether (2 ×10 mL) and ethyl acetate(3 ×10 mL). The combined organic layers were dried over Na2SO4, filtered and evaporated under reduced pressure. The crude material was purified by column chromatography on silica gel with pentane/diethylether (100:0 to 70:30) as eluent to afford the pure title compound

At the same time, in my other blogs, there are other synthetic methods of this type of compound,41288-96-4, 2-Chloro-5-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Article; Landelle, Gregory; Schmitt, Etienne; Panossian, Armen; Vors, Jean-Pierre; Pazenok, Sergiy; Jeschke, Peter; Gutbrod, Oliver; Leroux, Frederic R.; Journal of Fluorine Chemistry; vol. 203; (2017); p. 155 – 165;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem