Tag: M.W:100-200

Application of 696-42-4, 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. 696-42-4, name is 5-Fluoronicotinonitrile. A new synthetic method of this compound is introduced below.

A mixture of 5-fluoropyridine-3-carbonitrile (1 g, 6.55 mmol, 1 eq) and 4-methyl-lH-pyrazol-5- amine (707.02 mg, 6.55 mmol, 1 eq) in xylene (10 mL) was stirred at 70 C for 0.5 h. Then AlMe3 (2 M, 3.93 mL, 1.2 eq) was added to the mixture in one portion at 100 C. The mixture was stirred at 100 C for 16 h. The mixture was quenched with MeOH (30 mL) and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography (from DCM/MeOH = 1/0 to 5/1, TLC: DCM/MeOH = 5/1, Rf = 0.40) to yield product of 5-fluoro-N’-methyl-1H-pyrazol-5-yl)pyridine-3-carboxamidine (1.09 g, 3.86 mmol, 58.9% yield, 77.7% purity) as yellow oil. NMR (400 MHz, CD3OD) delta ppm 8.98 (s, 1H), 8.60 (d, J = 2.4 Hz, 1H), 7.38 (s, 1H), 7.17 (s, 1H), 2.14 (s, 3H); ES-LCMS m/z 220.2 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,696-42-4, 5-Fluoronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26493-11-8 ,Some common heterocyclic compound, 26493-11-8, molecular formula is C6H7N3OS, 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 intermediate 3 (8 g, 39.8 mmol), copper (II) bromide (10.43 g, 46.68 mmol) and 3-methyl-l-nitrosooxy-butane (6.8 g, 58.35 mmol) in ACN (100 mL) was stirred at room temperature for 1.5 hours. The solvent was evaporated in vacuo. The residue thus obtained was dissolved in AcOEt and washed with H20. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo to yield 5 g (55%) of intermediate 4 that was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,26493-11-8, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MACDONALD, Gregor, James; TRABANCO-SUAREZ, Andres, Avelino; CONDE-CEIDE, Susana; TRESADERN, Gary, John; BARTOLOME-NEBREDA, Jose, Manuel; PASTOR-FERNANDEZ, Joaquin; WO2011/73339; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 61494-55-1, 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 61494-55-1 as follows.

Acetyl chloride (0.651 mL, 9.16 mmol) was added to a suspension of (2- chloropyridin-3-yl)acetic acid (1117) (1.048 g, 6.108 mmol) in MeOH (30 mL). The mixture was heated at reflux for 20 hours. The volatiles were removed in vacuo and the residue partitioned between OCM (100 mL) and sat. NaHC03 ( 100 mL). The layers were separated and the aqueous layer extracted with DCM (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2S0 ) and the solvent removed under reduced pressure to yield an oil which was purified by column chromatography on silica gel (0-40% EtOAc in petroleum benzine 40-60 C) to afford the title compound (1118) (0.863 g, 76%) as a pale yellow oil; NMR (400 MHz, dr D SO) delta 8.34 (dd, J = 4.8, 1.9 Hz, H), 7.88 (dd, J – 7.5, 1.9 Hz, 1 H), 7.43 (dd, J.= 7.5, 4.8 Hz, 1 H), 3.86 (s, 2H), 3.65 (s, 3H). LCMS Method C: rt 5.04 min; m/z 186 [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,61494-55-1, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 189230-41-9, 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 189230-41-9, name is 2-Bromopyridine-3,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To a solution of 2-fluoro-6-iodobenzaldehyde (1.5 g, 6.0 mmol) and 2-bromopyridine-3,4-diamine (1.1 g, 6.0 mmol) in ethanol (20 mL), was added ferric chloride (778 mg, 4.80 mmol). The reaction mixture was stirred at 60 C. under oxygen atmosphere overnight. The next day, solvent was evaporated via rotavap and theresulting residue was purified by column chromatography on silica gel eluting with petroleum/ethyl acetate (3:1) to give the desired product (1.6 g, 64% yield) as a yellow solid. LCMS (ESI) m/z: 418 [M+H+].

According to the analysis of related databases, 189230-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Lai, Yingjie; Liang, Jun; Magnuson, Steven R.; Robarge, Kirk D.; Tsui, Vickie H.; Zhang, Birong; US2014/206702; (2014); 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, the common compound, a new synthetic route is introduced below. Product Details of 61494-55-1

To 30 ml of a THF solution containing 700 mg of 2-(2-chloropyridin-3-yl)acetic acid was added dropwise 7.75 ml of a 1.9 mol/L THF solution of hexamethyldisilazane sodium at -78 C. and the mixture was stirred for 10 minutes. Then, 616 mul of methyl 2,6-difluorobenzoate was added dropwise thereto, and then, the temperature of the mixture was raised from -78 C. to room temperature and stirred for 1 hour. To the mixture was added an aqueous saturated ammonium chloride solution followed by stirring the mixture for 1 hour. Thereafter, ethyl acetate was added thereto and the liquids were separated. The obtained organic layer was washed with saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 450 mg of a transparent oily product. (1215) 1H-NMR (CDCl3) delta: 8.35 (1H, dd, J=4.7, 1.8 Hz), 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.44-7.43 (1H, m), 7.25 (2H, dd, J=7.6, 4.7 Hz), 7.00-6.96 (2H, m).

The synthetic route of 61494-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUI CHEMICALS AGRO, INC.; UMETANI, Hideki; OKAYA, Shun; IKISHIMA, Hideaki; FUKUMOTO, Takeshi; NISHIDA, Akihiro; YANAGI, Masanori; NAITO, Ryohei; MASUTOMI, Koji; SHIRAKAWA, Tomomi; SAKURADA, Akane; YUTANI, Satoshi; (368 pag.)US2020/45968; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1443-42-1, 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 1443-42-1 as follows.

General procedure: Example 6A (2 g, 6.35 mmol) and (4-fluorophenyl)methanamine (0.794 g, 6.35 mmol) in acetonitrile (10 ml) were stirred at 120 C overnight. The reaction mixture was cooled, concentrated, taken into ethyl acetate and washed with saturated aqueous NaHC03 and brine. The combined aqueous layers were extracted twice with ethyl acetate. The combined organic extracts were dried (MgS04) and filtered. The filtrate was concentrated until solid material precipitated. The mixture was filtered to provide the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1443-42-1, its application will become more common.

Reference:
Patent; ABBVIE INC.; SWEIS, Ramzi F.; CURTIN, Michael L.; PLIUSHCHEV, Marina A.; HANSEN, Todd M.; LONGENECKER, Kenton; WO2013/170118; (2013); 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. 67310-56-9, name is 1-(5-Hydroxypyridin-2-yl)ethanone, molecular formula is C7H7NO2, 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. SDS of cas: 67310-56-9

Example 136: 2-[(6-acetylpyridin-3-yl)oxy]-iV-{3-[2-(4-chloro-3- fluorophenoxy)acetamido] 0-bicyclo [ 1.1.1] pentan- 1-yl {acetamide (Compound 235) A 2.5 mL microwave vial was charged with Example 28A (35 mg, 1 equivalent, 0.096 mmol), K2C03 (27mg, 0.19 mmol), l-(5-hydroxypyridin-2-yl)ethanone (27 mg, 0.19 mmol) and potassium iodide (1,2 mg, 0.07 equivalent, 0.05 mmol). To this mixture was added acetone (1.5 mL). The resulting mixture was heated in a Biotage Initiator microwave for 45 minutes at 140 C (0-450 W). Upon completion, the mixture was then filtered, and the filtrate was concentrated to dryness. The residue was dissolved in 1 : 1 dimethyl sulfoxide/methanol and purified by preparative reverse phase HPLC on a Phenomenex Luna C8(2) 5 muiotatauiota 100 A AXIA column (30 mm chi 150mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-0.5 minutes 5% A, 0.5-8.5 minutes linear gradient 5-100% A, 8.7-10.7 minutes 100% A, 10.7 -11.0 minutes linear gradient 100-5% A) to afford the title compound. XH NMR (400 MHz, DMSO-c) delta ppm 8.39 (d, J = 2.9 Hz, 1H), 7.96 (d, J = 8.8 Hz, 1H), 7.53 – 7.45 (m, 2H), 7.05 (dd, J = 11.3, 2.9 Hz, 1H), 6.85 (ddd, J = 9.0, 2.8, 1.2 Hz, 1H), 4.64 (s, 2H), 4.46 (s, 2H), 2.58 (s, 3H), 2.28 (s, 6H). MS (APCI) m/z 462.3 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 67310-56-9.

Reference:
Patent; CALICO LIFE SCIENCES; ABBVIE, INC.; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina; FROST, Jennifer, M.; BLACK, Lawrence, A.; XU, Xiangdong; SWEIS, Ramzi, Farath; SHI, Lei; ZHANG, Qinwei, I.; TONG, Yunsong; HUTCHINS, Charles, W.; CHUNG, Seungwon; DART, Michael, J.; (445 pag.)WO2017/193034; (2017); 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. 84487-03-6, name is 6-Chloro-5-nitropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-Chloro-5-nitropyridin-2-amine

REFERENCE EXAMPLE 2 Preparation of the starting compound 6-Amino-2-chloro-3-nitropyridine was allowed to react with ethanethiol to give 6-amino-2-ethylthio-3-nitropyridine (m.p. 131.5-132 C.).

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, 84487-03-6, 6-Chloro-5-nitropyridin-2-amine.

Reference:
Patent; Dainippon Pharmaceutical Co., Ltd.; Laboratoire Roger Bellon; US4382937; (1983); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 85148-95-4, 6-Formylpicolinonitrile, 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, 85148-95-4, blongs to pyridine-derivatives compound. name: 6-Formylpicolinonitrile

(a) 2-Amidino-6-formylpyridine hydrochloride 2-Cyano-6-formylpyridine (16.5 g =0.125 mol) is dissolved in 150 ml of dry ether and 150 ml of absolute ethanol, and the solution is saturated at 0° with dry hydrochloric acid gas and left to stand at 0° for 44 hours. The reddish brown reaction solution is concentrated to dryness. In order to remove excess hydrochloric acid, the residue is re-dissolved in absolute ethanol, concentrated by evaporation again and finally dried under a high vacuum. The resulting crude imino ether is dissolved in 100 ml of absolute ethanol, and a saturated ethanolic ammonia solution (100 ml) is added thereto. The reaction mixture is heated under reflux for 3 hours, cooled, filtered until clear and the filtrate is concentrated by evaporation. The solution of the residue in 100 ml of 2N hydrochloric acid is washed with ether, concentrated to dryness by evaporation and dried under a high vacuum. The title compound is obtained in crude form which is further processed direct.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,85148-95-4, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4971986; (1990); A;; ; Patent; Ciba-Geigy Corporation; US5238941; (1993); A;,
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. 630395-95-8, name is 1H-Pyrrolo[3,2-c]pyridine-2-carbaldehyde, molecular formula is C8H6N2O, 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. COA of Formula: C8H6N2O

1H-Pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester, 5b-1 (Scheme 3, step j) Add to a 0 C. solution of 1H-pyrrolo[3,2-c]pyridine-2-carboxaldehyde (9b-1, 3.24 g, 22.19 mmol) in methanol under argon, sodium cyanide (5.44 g, 111 mmol) and manganese dioxide (9.65 g, 111 mmol). Stir the reaction mixture for 5 h, filter through Celite and dilute with 500 ml EtOAc. Wash the organic layer with water (2*) and brine, dry over sodium carbonate, filter, and concentrate to provide the title compound (3.27 g) as a pure tan solid.

With the rapid development of chemical substances, we look forward to future research findings about 630395-95-8.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/131012; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem