Tag: M.W:100-200

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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H6N2O2

To a solution of 4-bromoaniline (200 mg, 1.16 mmol, 1 eq) in EtOAc (5 mL) was added 2-methylpyrazole-3-carboxylic acid (175.95 mg, 1.40 mmol, 1.2 eq), DIEA (450.78 mg, 3.49 mmol, 607.52 muL, 3 eq) and T3P (2.22 g, 3.49 mmol, 2.07 mL, 3 eq). The mixture was stirred at 60 C. for 12 h. Sat. NaHCO3 solution (10 mL) was added and the mixture was extracted with ethyl acetate (10 mL*3). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to afford the crude product which was purified on silica gel column chromatography (from PE/EtOAc=1/0 to 3/1, TLC: PE/EtOAc=2/1, Rf=0.47) to give N-(4-bromophenyl)-2-methyl-pyrazole-3-carboxamide (198 mg, 699.77 mumol, 60.2% yield, 99.0% purity) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.61 (s, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.47 (s, 4H), 6.63 (d, J=2.0 Hz, 1H), 4.20 (s, 3H); ES-LCMS m/z 279.6 [M+H]+.

According to the analysis of related databases, 16034-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 15366-34-4, These common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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 3-[5-(bromomethyl)-2-thienyl]-5-(trifluoromethyl)-1 ,2,4-oxadiazole (1.0 g, 3.2 mmol), methyl 1 H-pyrazole-3-carboxylate (600 mg, 4.8 mmol) and potassium carbonate (880 mg, 6.4mmol) in acetonitrile (32 mL) was heated at 1 10C for 2 hours. The orange suspension was filtered to remove the solids and the filtrate solution was then concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography on silica gel using a cyclohexane/ethyl acetate gradient to afford 610 mg of the title compound as a white solid. LC/MS (Method A) retention time = 1.00 minutes, 359 (M+H). 1NMR (400 MHz, CDCI3) delta ppm: 7.78 (d, 1 H), 7.51 (d, 1 H), 7.12 (d, 1 H), 6.89 (d, 1 H), 5.61 (s, 2H), 3.98 (s, 3H). methyl 2-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-3-carboxylate (Compound 1.54 of Table T1 ) was isolated as a byproduct in form of a white solid (274 mg). LC/MS (Method A) retention time = 1.10 minutes, 359 M+H).

The synthetic route of 15366-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; PITTERNA, Thomas; RAJAN, Ramya; (0 pag.)WO2018/158365; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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. COA of Formula: C4H4ClN3O2

KO’Bu (938 mg, 8.36 mmol) was added to a stirred solution of 5-chloro-l-methyl-4- nitro-lH-pyrazole (900 mg, 5.57 mmol) and cyclopropanol (970.713 mg, 16.713 mmol) in MeCN (7.27 mL) at rt. Addition was done portionwise. The mixture was stirred at rt for 3hours. Water was added and the mixture acidified with 3N HCl(aq). The reaction mixture was extracted with DCM, dried over MgS04, filtered and evaporated. A purification was performed via preparative LC (Stationary phase: irregular SiOH 15- 40muiotaeta 80g GraceResolv, Mobile phase: gradient from 100% DCM to 98% DCM, 2% MeOH, 0, 1% NH4OH) to afford intermediate 620 (470 mg, yield 46 %).

The synthetic route of 5-Chloro-1-methyl-4-nitro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 71229-85-1,Some common heterocyclic compound, 71229-85-1, name is 4-Bromo-1-ethyl-1H-pyrazole, molecular formula is C5H7BrN2, 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.

In a nitrogen atmosphere, a mixture of 1.62 g of 4-methoxy-3-methyl-phenylboronic acid, 1.57 g of 4-bromo-1-ethyl-1H-pyrazole (9X), 0.79 g of a 1,1?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex, 3.51 g of sodium carbonate, 100 ml of 1, 4-dioxane, and 30 ml of water was stirred with heating under reflux for 4 hours. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.3 g of 9Y represented by the following formula.

The synthetic route of 71229-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; DOTA, Koichiro; (92 pag.)US2017/105415; (2017); 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. 34605-66-8, name is 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C10H13N3

Step 2) 2-(3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazol-5-yl)propan-2-ol At -78 C., to a solution of 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole (708.5 mg, 4.04 mmol) in THF (8 mL) was added n-BuLi (2.4 M in THF, 2.5 mL, 6.00 mmol) dropwise. The reaction mixture was continued to stir at -78 C. for 0.5 h and then move to 0 C. for 2 h. Acetone (362.1 mg, 6.24 mmol) was added to the solution. The reaction mixture was stirred at rt for 3 h, quenched with water (20 mL), and extracted with EtOAc (50 mL*3). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the title compound as yellow oil (353.0 mg, yield 37.4%). LC-MS (ESI, pos. ion) m/z: 234.4 [M+H]+; 1H NMR (400 MHz, CDCl3): delta (ppm) 5.99 (s, 1H), 5.85 (s, 2H), 4.10 (s, 3H), 2.12 (s, 6H), 1.88 (br. s, 1H), 1.70 (s, 6H).

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:
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (78 pag.)US2016/229837; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2458-26-6, name is 3-Phenyl-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 2458-26-6, SDS of cas: 2458-26-6

NaH (4.3mg, 0.18mmol) was added to a solution of 15 (42mg, 0.09mmol) and 3-phenyl-pyrazol (38.9mg, 0.27mmol) in DMF (1mL). The solution was heated at 130C for 30min using microwave heating. The reaction was quenched with saturated NaHCO3 (10mL) and EtOAc (15mL) was added. The phases were separated and the organic phase extracted with NaHCO3 (10mL) and concentrated. Yield: 60mg of the crude intermediate (2R,4aR,10aR)-9-methoxy-2-(3-phenyl-pyrazol-1-ylmethyl)-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine. LC/MS: ELSD: 99.9%; UV: 71.5%; MH+ 418.1.

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, 3-Phenyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Risgaard, Rune; Jensen, Martin; J°rgensen, Morten; Bang-Andersen, Benny; Christoffersen, Claus T.; Jensen, Klaus G.; Kristensen, Jesper L.; Pueschl, Ask; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 381 – 392;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 20583-33-9, The chemical industry reduces the impact on the environment during synthesis 20583-33-9, name is 1-(1H-Pyrazol-3-yl)ethanone, I believe this compound will play a more active role in future production and life.

Pyrazole viii (20 g, 0.18 mol) is dissolved in dimethylformamide (DMF) (300 mL), and cesium carbonate (70 g, 0.22 mol) is added, followed by tosylate xxvii (45 g, 0.19 mol). The mixture is stirred for 12 hours, then poured into ice cold water and extracted into ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and concentrated. The residue is purified by flash column chromatography (10% ethyl acetate in petroleum ether) to give difluoride xxviii (2.56 g, 0.15 mol) in 83% yield.

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, 1-(1H-Pyrazol-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CLAVIUS PHARMACEUTICALS, LLC; SAWYER, J. Scott; (132 pag.)WO2020/41562; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 56984-32-8, 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. 56984-32-8 name is Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, This 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.

C. 5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid 5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid, ethyl ester (13 grams, 0.07 mole) and potassium hydroxide (7.8 grams, 0.14 mole) were combined in 75 ml. of ethanol and refluxed for six hours. The solution was cooled, poured over water, acidified with concentrated hydrochloric acid, and the precipitated solid collected, dried, and recrystallized from water. The resulting 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid was obtained in the amount of 5.4 grams and melted at 195-197 C. Analysis calculated for C5 H5 ClN2 O2 Theory: C, 37.53; H, 3.15; N, 17.15; Found: C, 37.68; H, 3.06; N, 17.69.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US4620865; (1986); A;,
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. 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Phenylpyrazole-4-carboxaldehyde

General procedure: To a well stirred mixture of 2,6-difluoro-3-aminobenzamide(10) (0.17 g, 1.0 mmol) and 3-n-butoxybenzaldehyde (0.17 g,1.0 mmol) in MeOH (10 mL) at 0 C, was added p-toluenesulfonicacid monohydrate (0.02 g, 0.11 mmol) and the reaction mixturewasstirred for 2 h. After that, excess sodium cyanoborohydride (0.63 g,10.0 mmol)was added in portions to the reaction mixture. After theaddition, the reaction mixture was stirred for further 12 h. The reactionwas quenched by pouring into a separating funnel containing50 mL water and extracted with ethyl acetate (20 mL x 3). Thecombined organic layers were dried over MgSO4, filtered andevaporated under reduced pressure to a crude product, which wassubjected to purification by flash column chromatography on silicagel with gradient elution (20%e50% ethyl acetate in hexane) toafford the titled compound (0.15 g) in 45% yield.

The synthetic route of 54605-72-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lui, Hok Kiu; Gao, Wei; Cheung, Kwan Choi; Jin, Wen Bin; Sun, Ning; Kan, Jason W.Y.; Wong, Iris L.K.; Chiou, Jiachi; Lin, Dachuan; Chan, Edward W.C.; Leung, Yun-Chung; Chan, Tak Hang; Chen, Sheng; Chan, Kin-Fai; Wong, Kwok-Yin; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 95 – 115;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7119-95-1, name is 1-Nitropyrazole, molecular formula is C3H3N3O2, 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. category: pyrazoles-derivatives

A solution of 1-nitro-1H-pyrazole (4.00 g, 35.4 mmol) in 40 mL of benzonitrile was refluxed for 2 h. After being cooled to 25 C., the mixture was poured into 160 mL of hexanes. A white solid precipitated which was filtered and dried in vacuo, to afford 3-nitro-1H-pyrazole (3.16 g, 79%). H1-NMR (400 MHz, DMSO-d6) delta: 7.01 (1H, d, J=2.4 Hz), 8.01 (d, 1H, J=3.4 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7119-95-1, its application will become more common.

Reference:
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Sarabu, Ramakanth; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/21032; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics