Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 70951-85-8, name is 4-Bromo-1-(tert-butyl)-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 70951-85-8, HPLC of Formula: C7H11BrN2

Stage d) Preparation of 1-(1,1-Dimethylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 11) To a 20 L four-neck bottle, 4-bromo-(tert-butyl)pyrazole (1.15 kg, 5.66 mol) and THF (9.2 L) were added, then the mixture was cooled to between -78 C. and -85 C. and treated with nBuLi (6.23 mol) dropwise at that temperature. After addition the solution was stirred at the same temperature for 1 h and isopropyl pinacol borate (1.47 kg, 7.92 mol) was added dropwise. The reaction was complete after stirring for ?3 h (starting material<1.0% a/a by GC) then water (2.3 L) was added to quench the reaction; and the pH adjusted to 8-9 by addition of 3.45 kg 1M HCl. The aqueous phase was extracted with TBME (3.45 L*2), and the combined organic phase washed with 5% NaCl (3.45 L*2) and water (3.45 L) in sequence. The organic phase was evaporated to give the crude product. After subsequent recrystallization from heptanes the pure product was obtained as a white solid (GC purity 99.7% a/a) in a 63.5% th overall yield. (Two 20 L reactions were run, then combined in the heptane recrystallization). 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; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander George Steven; Wilson, David Matthew; US2013/40984; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 51516-70-2, The chemical industry reduces the impact on the environment during synthesis 51516-70-2, name is 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

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, 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 16078-71-0, 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. 16078-71-0, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

[00139] A solution of 1 ,2-bis-(4-chloro-phenyl)-ethanone (lOOmg, 0.38 mmol) in dichloroethane (1 mL) is stirred at room temperature while TiCl4 (143 mg, 0.75 mmol) is added in dropwise. After the addition, the mixture is stirred at room temperature for 5 min and a solution of 5-amino-l-phenyl-lH-pyrazole-4-carboxilic acid ethyl ester (97 mg, 0.42 mmol) in dichloroethane (1 mL) is added dropwise. After the addition, the EPO mixture is heated to 125 0C for 5 h. After cooling down the mixture, it is poured into a mixture of ice cold saturated aqueous NaHCO3 solution (15 mL) and EtOAc (15 mL). The resulted mixture is filtered through celite to remove the precipitate and washed with EtOAc (2×5 mL). The filtrate is extracted by EtOAc (3*5 mL). The organic layers are combined and washed with brine and dried (MgSO4). After filtering off the drying agent, the filtrate is concentrated and purified by preparative LC/MS to provide the titled compound 5,6-bis-(4-chloro-phenyl)-l-phenyl-lH-pyrazolo[3,4-b]pyridin-4-ol as light yellow solid.(55 mg, 31%). 1H NMR (MeOD) delta(ppm) 8.37(s, IH), 8.23 (d, 2H), 7.53 (t, 2H), 7.34(t, IH), 7.31 (d, 2H), 7.29 (d, 2H), 7.23 (d, 2H), 7.15 (d, 2H); HPLC-MS calculated for C24H15Ci2N3O (M+l+): 432.1, found: 432.2.

The chemical industry reduces the impact on the environment during synthesis Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IRM LLC; WO2006/47516; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37687-24-4,Some common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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.

Preparation of Intermediate 1-12.A mixture of Intermediate 1-13 (1.21 g, 2.65 mmol), diethyl 3,5- pyrazoledicarboxylate (539 mg, 2.54 mmol) and K2C03 (440 mg, 3.18 mmol) in acetone (20 mL) was stirred overnight at rt. Water (50 mL) was added and the mixture was extracted with DCM (4 x 150 mL). The combined organic layers were washed with brine (50 mL), dried (MgS04), filtered and evaporated. The residue was purified by column chromatography (EtOAc:cyclohexane, 30:70) and the product obtained was triturated from Et20 to give the desired product (898 mg, 66%) as a white solid.1H N R (300 MHz, DMSO) delta 9.02 (s, 2H), 7.34 (s, 1 H), 7.22 (d, J = 8.6 Hz, 4H), 6.89 (d, J = 8.7 Hz, 4H), 6.14 (s, 2H), 4.83 (s, 4H), 4.31 (q, J = 7.1 Hz, 2H), 4.23 (q, J = 7.1 Hz, 2H), 3.73 (s, 6H), 1.31 (t, J = 7.1 Hz, 3H), 1.22 (t, J = 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 3,5-pyrazoledicarboxylate, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALES, Sonia; RODRIGUEZ HERGUETA, Antonio; RAMOS LIMA, Francisco, Javier; ALVAREZ ESCOBAR, Rosa, Maria; HIGUERAS HERNANDEZ, Ana Isabel; WO2011/141713; (2011); 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. 63874-99-7, name is 1-(4-Chlorophenyl)-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 63874-99-7

General procedure: 5 mmol 1-Arylpyrazole-4-carbaldehyde, 5 mmol 2-methyl-8-hydroxyl quinoline and 20 mL acetic anhydride were stirred and sealed in a Teflon-lined stainless steel autoclave (25 mL), kept at 160 C for 4 days and then cooled to room temperature. Resultant mixed solution was poured into 100 mL H2O, followed by extractionwith CH2Cl2 (3 50 mL) and rotary evaporation to remove solvent. As-separated crystalline precipitates were dissolved in 25 mL DMF, followed by dropwise addition of 20 mL of aqueous HCl (volume fraction: 36%) at 80 C in a reaction period of 5 h. Then the reactants were allowed to react for additional 4 h after 25 mL of triethylamine was added dropwise. Upon completion of the reaction, the hot mixture was poured into ice water (250 mL) and stirred overnight, followed by extraction with CH2Cl2 (4 100 mL).The combined organic layers were washed with saturated NaCl solution and dried with anhydrous Na2SO4. Crude mixed products were obtained after residual solvent was evaporated under reduced pressure, and as-obtained crude products were purified by column chromatography (silica gel, ethyl acetate/petroleum ether).

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; Ren, Tiegang; Wang, Jie; Li, Guihui; Cheng, Hongbin; Li, Yongzhe; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 129; (2014); p. 7 – 13;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1082745-50-3,Some common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, molecular formula is C9H14N4O2, 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.

To a solution of 0.8 g (3.805 mmol) of 5-amino-l-(tetrahydro-pyran-4-yl)-l-H-pyrazole-4- carboxylic acid amide (see PCT patent application WO2010/026214) in 8 mL anhydrous EtOH , 0.457 g (19.6 mmol) of sodium hydride (60 % suspension in mineral oil) were added at room temperature under nitrogen. After 1 h under stirring, 1.2g (11.42mmol) of trans- cyclobutane-l,2-dicarbonitrile were added and the reaction mixture was heated to 140C for 45 min in a microwave oven. The solvent was removed under reduced pressure. The residue was dissolved in DCM, water was added and phases were separated. Organic layers were dried over sodium sulphate and evaporated under reduced pressure. The crude was purified by flash cromatography (Cy/EtOAc from 80/20 to 100%) to obtain the title compound as yellow solid. (0.64g, 55%)HPLC-MS(MethodlEh):R,=6.21minMS (APCI): m/z = 300 (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 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-iodo-l-methyl-lH-pyrazole (23.31 mg, 0.112 mmol) in anhydrous DMSO (5 ml) was added intermediate 19.6-2 (20 mg, 0.075 mmol), (Irans)-N 1.N2-dimethylcycloheane- 1, 2-diamine (2.125 mg, 0.015 mmol), potassium phosphate (47.6 mg, 0.224 mmol), and Cul (1.423 mg, 7.47 pmol). The resulting mixture was stirred at 90C under N2 protection for 12 hours. Afterward, the crude reaction solution was filtered and concentrated. The crude material was purified by pre-HPLC (TFA) to give example 19.7-2, ( R,R or 5riV)-5-chloro-6-(3-nuoro- 1 – methylpiperidin-4-yl)-l-(l-methyl-lH-pyrazol-4-yl)-lH-indazole, TFA salt. MS (ESI) m/z calc?d for Ci7H20ClFN5 [M+H]+ 348, found 348. NMR (400 MHz, CD3OD) d 8.12-8.22 (m, 2H), 7.94 (s, 1H), 7.87 (s, 1H), 7.66 (s, 1H), 5.22-5.48 (m, 1H), 3.75-4.03 (m, 5H), 3.60 (m, 1H), 3.15-3.31 (m, 1H), 3.15-3.31 (m, 1H), 3.03 (s, 3H), 2.26 (br s, 1H), 2.10 (m, 1H). LRRK2 IC50 3.0 nM.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
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. 187998-35-2, name is 1-(4-Chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(4-Chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

To Example 1E (10 mg, 0.037 mniol) and 1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (13.7 mg, 0.0580 mmol) in DMF (880 mu), was added DIEA (46.0 mu, 0.264 mmol), followed by addition of BOP (25.7 mg, 0.0580 mmol). The reaction mixture was stirred at rt for 4 h then quenched by the addition of a few a drops of water, diluted with methanol, filtered and purified on preparative HPLC to yield Example 1 (11 mg, 44%) as a white powder. MS (ESI) m/z: 486.0, 1H NMR (500 MHz, DMSO-de) delta 8.20 (s, 1H), 7.92 (br s, 1H), 7.75- 7.43 (m, 3H), 7.33- 7.15 (m, 1H), 6.60 – 6.25 (m, 3H), 3.59 (br d, J=6.1 Hz, 2H), 3.19 (br s, 1H), 2.70 (s, 3H), 2.55 (s, 3H), 1.65 (d, J=6.8 Hz, 2H), 1.02 (d, J=6.3 Hz, 3H).

According to the analysis of related databases, 187998-35-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; LADZIATA, Vladimir; DE LUCCA, Indawati; TORA, George O.; MAISHAL, Tarun Kumar; TANGIRALA, Raghuram; THIYAGARAJAN, Kamalraj; (216 pag.)WO2019/14308; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 92525-10-5, 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. 92525-10-5 name is 3-Iodo-1-methyl-1H-pyrazole, 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.

A suspension of 3 ,3-dimethyl-6- (4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one (200 mg) and 5-bromo-2-methylpyrimidine (181 mg) in 1,4-dioxane (2 ml) and aqueous sodiumcarbonate (2 M) was flushed with argon, then [1,1?-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (26 mg) was added and stirring was continued at 115 C for 3 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 10% MeOH in dichloromethane) to give the title compound (148 mg, 84%) as a brown solid. MS (mlz): 254.2 [(M+H) :_The title compound was prepared in analogy to example ic using 3,3-dimethyl-6-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin-2-one from example lb and 3-iodo- i-methyl-i Hpyrazole to give the title compound (26%) as an off-white solid. MS (mlz): 242.1 [(M+H)?i.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 2033-45-6, 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. 2033-45-6, name is 3,5-Dimethyl-4-iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 79 (3OOg, 135 immol) in 100 mL of degassed TI-IF was added successively Cul(257mg, i.35mmoi), 2 (2.65g, 27O2mmoi), Pd(PPh3)2C12 (948mg, i.35mmol) and Et3N (410g.40.54rnmol). The mixture was stirred at 80 C for 18 hours. LCM showed that the reaction was completed. The reaction mixture was filtered and the filtrate was concentrated and purified by chrornatograph column to give the product 80 (2.2 g, yield 85%).LCMS: in/z 193 (M+H)t

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, 3,5-Dimethyl-4-iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics