Tag: M.W:100-200

Synthetic Route of 701-44-0, 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. 701-44-0, name is 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxamide. A new synthetic method of this compound is introduced below.

To a stirred solution of l-methyl-6-oxo-l,6-dihydropyridine-3-carboxamide (460 mg, 3.02 mmol) in 20 mL of CH2C12 was added TEA (0.548 mL, 3.93 mmol) at 0 C. The reaction mixture was stirred for 10 min and then triflic anhydride was added (1.0 M in CH2C12, 3.33 mL, 3.33 mmol). Removed ice bath and stirred at ambient temperature for 3 h. The reaction was quenched with water and saturated aqueous sodium chloride. The aqueous layer was extracted with CH2C12 (3x’s). The combined organic layers were then dried over sodium sulfate and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes: ethyl acetate (95:5 to 15:85), to give the title compound. MS: m/z = 135.0 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,701-44-0, 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CROWLEY, Brendan; FRALEY, Mark; POTTEIGER, Craig; LIM, John; SHERER, Ed; YU, Younong; MITCHELL, Helen; BIFTU, Tesfaye; NAIR, Anilkumar; WANG, Cheng; YANG, De-Yi; ZHU, Cheng; KAR, Nam Fung; HUANG, Xianhai; CHEN, Lei; ZHOU, Wei; PARK, Min, K.; CAI, Jiaqiang; WO2015/161014; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13958-86-6, 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 13958-86-6, name is 5-Methylpyridine-3,4-diamine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-methylpyridine-3,4-diamine (100 mg, 0.81.2 mmol) and N,N dimethylpyridin-4-amine (109 mg, 0.893 mmol) in MeCN was added di(l H-imidazol-1-yl)methanethione (217 mg, 1.218 mmol) portionwise. The mixture was stirred at room temperature for 4 h. The precipitate formed was filtered, washed with water, Et2O, DCM and dried to give 7-methyl-1H-imidazo[4,5-c]pyridine-2(3H)-thione (100 mg, 75% yield) as a pale red solid. 1H-NMR (400 MHz, DMSO-d6) delta ppm 12.73 (brs, 2H), 8.20 (s, 1H), 8.06 (s, 1H), 2.33 (s, 3H); ESI-MS: m/z 165.84 (M+H)+.

According to the analysis of related databases, 13958-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Stingray Therapeutics, Inc.; Vankayalapati, Hariprasad; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (117 pag.)US2020/39979; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1133879-69-2, 3-Fluoro-5-vinylpyridine, 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, name: 3-Fluoro-5-vinylpyridine, blongs to pyridine-derivatives compound. name: 3-Fluoro-5-vinylpyridine

General procedure: A mixture of tetrahydrocarbazole 5a (0.17 g,1 mmol), 5fluoro3vinylpyridine (6) (0.12 g, 1 mmol), CsF(0.1 g), and hydroquinone (0.02 g) in DMSO (1.5 mL) was heated with stirring at 130-140 C for 4 h, DMSO was evaporatedin vacuo (3 Torr), the product was extracted from residue withdichloromethane. The solvent was evaporated and the residuewas subjected to chromatography on silica gel (60 mesh), eluentmethanol-chloroform = 1 : 5. The yield was 0.22 g (75%), m.p.65-67 C. Found (%): C, 77.63; H, 6.43; N, 9.64. C19H19FN2.Calculated (%): C, 77.52; H, 6.45; N, 9.52. 1H NMR (DMSOd6), : 1.81 (m, 4 H, CH2); 2.29 (m, 2 H, CH2); 2.72 (m, 2 H,CH2); 3.05 (t, 2 H, CH2Py, J = 6.8 Hz); 4.25 (t, 2 H, CH2N,J = 6.9 Hz); 6.80 (dt, 1 H, CHPy, JHF = 9.3 Hz, JHH = 2.4 Hz);7.05-7.30 (m, 3 H, CHAr); 7.50 (d, 1 H, CHAr, J = 6.8 Hz); 8.14(s, 1 H, CHPy); 8.34 (d, 1 H, CHPy, JHH = 2.4 Hz). 19F NMR(DMSOd6), : -49.38 (d, JFH = 9.4 Hz).

The synthetic route of 1133879-69-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sokolov; Aksinenko; Nikolaeva; Grigor’Ev; Kinzirsky; Bachurin; Russian Chemical Bulletin; vol. 63; 5; (2014); p. 1137 – 1141; Izv. Akad. Nauk, Ser. Khim.; 5; (2014); p. 1137 – 1141,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60753-14-2 ,Some common heterocyclic compound, 60753-14-2, molecular formula is C9H13NO, 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.

7.561 g (0.05 mol) of 4-(3-pyridyl)-1-butanol and 19.020 g (0.05 mol) of 1-iodooctadecane were added to a three-necked flask.Add 70 ml of N,N-dimethylformamide,Then at 120 C,Stir the reaction for 12 hours,Cool to room temperature,After the reaction is over,Purifying the reaction product,After completely removing the monomer not involved in the reaction,Vacuum drying to constant weight,getIodinated 1-octadecyl-3-pyridinium butanol quaternary ammonium salt.

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. 60753-14-2, 4-(Pyridin-3-yl)butan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; South China University of Technology; Liu Fang; He Jingwei; Zhang Yunlong; (13 pag.)CN108484487; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886365-46-4 ,Some common heterocyclic compound, 886365-46-4, molecular formula is C7H6ClNO2, 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.

Step 2: N-(3-((4S,6S)-2-benzamido-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methylpicolinamide (rac-4-n) A round-bottomed flask was charged with N-((4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (rac-4l, 0.233 g, 0.589 mmol), DCM (8 mL), N,N-diisopropylethylamine (0.133 mL, 0.766 mmol), 5-chloro-3-methylpicolinic acid (intermediate 6) 0.131 g, 0.766 mmol) and finally with 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate; 0.347 mL, 0.589 mmol). The reaction mixture was stirred at room temperature for 15 min. The Reaction mixture was poured into aqueous saturated NaHCO3 (50 mL) and then extracted with EtOAc (2*50 mL). The combined extracts were washed with brine, dried over Na2SO4 and loaded onto silica gel. Purification by silica gel chromatography (gradient 0 to 30% EtOAc/hexane) gave the title compound (50 mg). MS m/z=549.1 [M+H]+. Calculated for C26H21ClF4N4O3: 548.9

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. 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (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 72093-04-0, name is 3-Chloro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H6ClN

To a mixture of 2-amino-N,N-dimethylbenzamide (1.3 g, 6.77 mmol), 3-chloro-4-methylpyridine (0.745 mL, 6.77 mmol), Palladium acetate (0.150 g) and BINAP (0.60 g) in 1,4-dioxane (10 mL) was added NaH (0.677 g, 16.93 mmol) and the resulting mixture was heated at 100 C. for 2 hours. The solvent was removed under reduced pressure. The residue obtained was taken into dichloromethane (50 mL) and filtered through celite. The filtrate was washed with water (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2) to provide 0.450 g of the desired product as a dark oil.

With the rapid development of chemical substances, we look forward to future research findings about 72093-04-0.

Reference:
Patent; ArQule, Inc.; US2010/249108; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 131747-62-1, 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.131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, molecular weight is 175.108, as common compound, the synthetic route is as follows.

Intermediate 1: (S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin- 2-yl)methanamine hydrochlorideStep 1. (S^)-2-Methyl-N-((3-(trifluoromethyl)pyridin-2-yl)methylene)- propane-2-sulfinamideTo a solution of 3-(trifluoromethyl)picolinaldehyde (Frontier Scientific, 9.80 g, 56.0 mmol) and DCM (50 mL) was added (5)-2-methylpropane-2- sulfinamide (AK Scientific, 10.3 g, 85.0 mmol) and copper(II) sulfate (35.3 g, 221 mmol). After 1.5 h at rt, the reaction was filtered through a pad of Celite brand filter agent and rinsed with DCM. The filtrate was concentrated in vacuo to give a dark green oil. The oil thus obtained was loaded onto a silica gel column and eluted with 30% EtOAc in hexanes to give (S,E)-2-methyl-N-((3-(trifluoro- methyl)pyridin-2-yl)methylene)propane-2-sulfinamide, as a golden oil. 1H NMR (delta ppm, CDCI3, 300 MHz): 9.02 (d, J = 4.3 Hz, 1H), 8.70 (d, J = 1.3 Hz, 1H), 8.38 (d, J = 7.7 Hz, 1H), 7.79 (dd, J = 7.9 & 4.8 Hz, 1H), 1.18 (s, 9H). MS (ESI pos. ion) m/z: 279.1 (M+H).

The chemical industry reduces the impact on the environment during synthesis 131747-62-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; BISWAS, Kaustav; BROWN, James; CHEN, Jian, J.; GORE, Vijay, Keshav; HARRIED, Scott; HORNE, Daniel, B.; KALLER, Matthew, R.; LIU, Qingyian; MA, Vu, Van; MONENSCHEIN, Holger; NGUYEN, Thomas, T.; YUAN, Chester, Chenguang; ZHONG, Wenge; ST. JEAN, David, J., Jr.; WO2012/177893; (2012); A2;,
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. 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., Safety of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

To compound 12 (200 mg, 1.07 mmol) and N,N-dimethylhydrazinecarbothioamide (153 mg, 1.28 mmol) was added a 1N aqueous sodium hydroxide solution (4.0mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The precipitate was collected by suction filtration and washed with water to yield 106 mg (40 %) of the title compound as a tan solid. 1H NMR (400 MHz, DMSO-d6): delta 3.18 (s, 6H), 7.36 (dd, J=8.0, 4.4Hz, 1H), 8.59 (dd, J=8.0, 1.5Hz, 1H), 8.63 (dd, J=4.4, 1.5Hz, 1H), 14.08 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 41.1, 111.4, 118.3, 130.8, 136.3, 150.0, 151.2, 152.4, 170.4. HRMS m/z calcd for C10H10N6S: 246.0688; found: 246.0680.

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, 956010-87-0, 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 863878-22-2, 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. 863878-22-2, name is 6-Chloro-4-methyl-3-nitropyridin-2-amine. A new synthetic method of this compound is introduced below.

Step 1 : (‘/?/)-(1-(6-Amino-4-methyl-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1 – yl)methanone (‘/?/)-(1 -(6-Amino-4-methyl-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone was prepared using a method analogous to the one used for Intermediate 2, Step 1 but using 6-chloro-4-methyl-3-nitropyridin-2-amine and (7?,)-piperidin-3-yl(pyrrolidin-1 – yl)methanone as starting materials. The reaction mixture was run at 70C for 1 h. MS (ES+APCI) (M+H) 333.9; LCMS retention time 4.322 min (Method Z).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,863878-22-2, 6-Chloro-4-methyl-3-nitropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; AHN, Kay; BOEHM, Markus; CABRAL, Shawn; CARPINO, Philip A.; FUTATSUGI, Kentaro; HEPWORTH, David; KUNG, Daniel W.; ORR, Suvi; WANG, Jian; WO2013/150416; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60186-15-4, 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. 60186-15-4, name is 2,4-Difluoro-5-nitropyridine. A new synthetic method of this compound is introduced below.

In a 250 mL round-bottomed flask vial was 2,4-difluoro-5-nitropyridine (1.035 g, 6.47 mmol) in tetrahydrofuran (30 mL) to give a tan solution. After cooling to -40 C, 1 -allylpiperazine (0.905 mL, 6.47 mmol) was added, followed by Et3N (1.802 mL, 12.93 mmol). The cloudy tan mixture was stirred at -40 C – -10C for 3 h. TLC (1/1 EtOAc/hexane) showed one major more polar yellow spot. The mixture was concentrated, and the residue was purified by FCC up to 80% EtOAc/hexane to afford the desired product (1.4347 g, 83%) as a yellow solid: 1H NMR (0112) (400 MHz, Chloroform-d) delta 8.58 (s, 1H), 6.41 (s, 1H), 5.97 – 5.77 (m, 1H), 5.31 – 5.1 (m, 2H), 3.33 – 3.23 (m, 4H), 3.09 (dt, J = 6.7, 1.3 Hz, 2H), 2.68 – 2.58 (m, 4H); 19F NMR (376 MHz, Chloroform-d) delta -62.07.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60186-15-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (45 pag.)WO2018/98413; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem