Tag: M.W:100-200

400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C6H7N3O4

10% palladium/C (2.87 g, 2.7 mmol) was added to a stirred solution of methyl 1 -methyl- 4-nitro-1 H-pyrazole-3-carboxylate (p69, 7.15 g, 38.6 mmol) in methanol (250 ml_) and stirred at RT under H2 atmosphere for 4 hrs. The catalyst was filtered off and the solvent was evaporated under vacuum to afford methyl 4-amino-1 -methyl-1 H-pyrazole- 3-carboxylate (p70, 6 g, y= quant) as purple wax used as such in the next step. MS (/T7/z): 156.1 [MH]+

The synthetic route of 400877-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; CREMONESI, Susanna; SEMERARO, Teresa; TARSI, Luca; GIBSON, Karl Richard; (116 pag.)WO2019/81939; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 25016-17-5, name is Methyl 5-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

b. Synthesis of I.S-dimethyl-pyrazole-delta-carboxylic acid methylester; S-methyl-pyrazole-delta-carboxylic acid methyl ester (6.8 Kg Kg) is dissolved in DMF (8L) and dimethyl sulfate (6.0 L) is added dropwise in over three hours. The reaction is exothermic and the addition of dimethyl sulfate must be controlled so that the internal temperature does not exceed 900C. After complete addition, the mixture is heated for 18 hours at 800C. The mixture is then cooled to room temperature, diluted with ice (3.4 Kg), and cooled in an ice bath. A solution of aqueous 28% ammonium hydroxide (8.6 L) is added to the reaction mixture over 3 hours. The resulting mixture is stirred for 18 hours, diluted with ethyl acetate (12 L) and water (16 L), extracted, and the layers are separated. The organic layer is washed with water (4L), dried over MgSO4, filtered, and concentrated under reduced pressure to provide 5.14 Kg of 1 ,3-dimethyl-pyrazole-delta-carboxylic acid methylester (69 % yield with a purity of >90 % by HPLC). The crude product is used directly in the next step.

The synthetic route of 25016-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2006/48761; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1151802-23-1, name is 4-Bromo-1-cyclopropyl-1H-pyrazole, belongs to pyrazoles-derivatives compound, 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 1151802-23-1, Application In Synthesis of 4-Bromo-1-cyclopropyl-1H-pyrazole

Step 1 : l-Cyclopropyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyridaziiie To a 100 n L flask is added 4-bromo-l-cyclopropylpyrazol (6.57 g, 35.1 mmol) and anhydrous THF (30 niL). The solution is cooled to -78 C under nitrogen; then n-butyl lithium (15.5 n L, 2.5 M in hexanes, 38.6 mmol) is added dropwise. The reaction mixture is stirred at the temperature for 1 hr, followed by addition of isopropyl boronate (9.17 g, 94.1 mmol) and stirred below -70 C for 3 hours. The reaction is quenched with water (20 n L) and the resulted mixture is adjusted to pH 8-9 with aqueous hydrochloride solution (1 N). The combined organic phases are concentrated and used in next step without further purification (6.64 g, 81% yield). (MS: [M+l] 235)

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.

Reference:
Patent; CROWN BIOSCIENCE INC. (TAICANG); ZHONG, Boyu; SHIH, Chuan; YUAN, Hongbin; ZHOU, Feng; WO2014/32498; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, belongs to pyrazoles-derivatives compound, 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 15366-34-4, Recommanded Product: 15366-34-4

c) Methyl l-cyclopropyl-lH-pyrazole-3-carboxylateMethyl lH-pyrazole-3-carboxylate (4 g, 31.7 mmol) was dissolved in di- chloroethane (160 ml). Na2C03 (6.72 g, 63.4 mmol) and cyclopropylboronic acid (5.44 g, 63.4 mmol) were added to the solution. The resulting mixture was heated to 70 C and a hot solution of bipyridine (4.92 g, 31.6 mmol) and Cu(OAc)2 (5.72 g, 31.6 mmol) in dichloroethane (40 ml) was added. The mixture was stirred at 70 C under an oxygen atmosphere overnight. Saturated aqueous solution of NaHC03 was added to the reaction mixture and extracted with EtOAc. The organic layer was evaporated and the residue was purified by flash chromatography. Yield 2.5 g. – NMR (400 MHz; DMSO-d6): delta 1.04-1.09 (m, 2H), 1.17-1.23 (m, 2H), 3.64-3.69 (m, IH), 3.91 (s, 3H), 6.78 (d, IH), 7.46 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1H-pyrazole-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 3112-31-0

A mixture of 31.7 g (0.203 mol) of diacid 1 and 125 mL of methanol was saturated with gaseous HCl. The mixture was refluxed for 3 h and left overnight at room temperature. The precipitate was filtered off and washed with methanol. Yield 23.5 g (63%), white crystals, mp 142-143C. IR spectrum, nu, cm-1: 3105 br (NH), 1710 s (C=O), 1240 s (C-O-C). 1H NMR spectrum, delta, ppm: 3.82 s (6H, CH3), 6.36 s (1H, 4-H), 14.43 s (1H, NH).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Kharaneko; Russian Journal of Organic Chemistry; vol. 52; 9; (2016); p. 1322 – 1325; Zh. Org. Khim.; vol. 52; 9; (2016); p. 1334 – 1337,4;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 72760-85-1, 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. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of pyrazole-imines 7 (1 mmol), aldehyde (1 mmol), TMSCN (1.2 mmol) in [Bmim]BF4 (0.5 g) was heated at 120 C for 24 h. After cooling, the reaction mixture was washed with water (5 mL) and the residue washed with MeOH to afford pure product 8.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Goli, Shokoufe; Mirzaei, Peiman; Bazgir, Ayoob; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2803 – 2809;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 10010-93-2,Some common heterocyclic compound, 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, molecular formula is C5H5F3N2, 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.

EXAMPLE 2. Preparation of N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-[(1R)-1-phenylpropyl]-4-thiazolecarboxamide (Compound 117) Step A: Preparation of 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-acetic acid. A mixture of 3-methyl-5-trifluoromethylpyrazole (10.0 g, 66.7 mmol), ethyl bromoacetate (11.1 mL, 100 mmol) and potassium carbonate (18.4 g, 133 mmol) in 80 mL of N,N-dimethylformamide was stirred at ambient temperature overnight. The orange mixture was filtered, diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give 15.7 g of the pyrazole ester. The ester, in 100 mL of tetrahydrofuran, was treated with 11 mL of a 50 % aqueous NaOH solution in 90 mL of water and stirred at ambient temperature overnight. The tetrahydrofuran was removed under reduced pressure and the aqueous solution was washed with ether and acidified with conc. HCl to pH 1 to give a precipitate. The precipitate was filtered, washed with water and dried to give 12.1 g of the title compound as a white solid. 1H NMR (Acetone-d6) delta 2.35 (s, 3H), 5.07 (s, 2H), 6.45 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/14290; (2007); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Ethyl 1H-pyrazole-3-carboxylate

To a solution of ethyl 1 H-pyrazole-3-carboxylate (2 g) in MeCN (40 ml) was added cesium carbonate (4.65 g) and the mixture stirred for 30 min when 4-(bromomethyl)tetrahydro-2H- pyran (2.81 g) was added and the mixture stirred at RT for 18 h. The solvent was removed in vacuo and the residue partitioned between dichloromethane (50 ml) and water (20 ml), separated by hydrophobic frit and concentrated. The filtrate was purified by silica (2 x 100 g) cartridge on Flashmaster II using a gradient of DCM and ethyl acetate to give the title compound 1 as a colourless oil, 0.944 g and title compound 2, as a colourless oil, 1 .026g.1 ; LCMS (method B); Rt = 0.90 min, MH+ = 239.2; LCMS (method B); Rt = 0.75 min, MH+ = 239.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5932-27-4.

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;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 63680-90-0, 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 63680-90-0 as follows.

Step 2: Preparation of tert-butyl (3-chloro-1H-pyrazol-4-yl)carbamate Into a 2 L round bottom flask was added 3-chloro-1H-pyrazol-4-amine hydrochloride (100 g, 649 mmol) and THF (500 mL). To this mixture were added di-tert-butyldicarbonate (156 g, 714 mmol) followed by sodium bicarbonate (120 g, 1429 mmol) and water (50.0 ml). The mixture was stirred for 16 h, diluted with water (500 mL) and ethyl acetate (500 mL) and transferred to a separatory funnel. This gave three layers; bottom-a white gelatinous precipitate, middle-light yellow aqueous, top-auburn organic. The phases were separated collecting the white gelatinous precipitate and the aqueous layer together. The aqueous was extracted with ethyl acetate (2*200 mL) and the ethyl acetate extracts were combined, washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered and rotary evaporated to give an auburn thick oil (160 g.). The thick oil was suspended in hexane (1000 mL) and stirred at 55 C. for 2 h. This gave a light brown suspension. The mixture was cooled to 0 C. and the solid collected by vacuum filtration and rinsed with hexane (2*10 mL). The sample was air dried to constant mass to afford (3-chloro-1H-pyrazol-4-yl)carbamate (102.97 g, 72% yield, 80% purity) as a light brown solid: mp 137-138 C.; 1H NMR (400 MHz, CDCl3) delta 10.69 (s, 1H), 7.91 (s, 1H), 1.52 (s, 9H).

According to the analysis of related databases, 63680-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; US2013/288893; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 948570-75-0, A common heterocyclic compound, 948570-75-0, name is 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole, molecular formula is C6H9N3O3, 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: To a solution of compound 19a (6.4 g, 50.0 mmol) and Pd/C (10 wt%, 0.6 g) in ethanol (50 mL) was stirred at room temperature under ahydrogen atmosphere for 2 days. The reaction mixture was then filteredthrough Celite and concentrated to provide

The synthetic route of 948570-75-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Cheng-Juan; Shu, Lei; Wang, Zhi-Jian; Yin, Yuan; Yu, Ru-Nan; Zhang, Da-Yong; Zhang, Tian-Tai; Bioorganic Chemistry; vol. 98; (2020);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics