Tag: M.W:100-200

Electric Literature of 360056-45-7,Some common heterocyclic compound, 360056-45-7, name is Methyl 4-amino-1H-pyrazole-3-carboxylate, molecular formula is C5H7N3O2, 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.

methyl 4-amino-1H-pyrazole-3-carboxylate (1.0 g, 7.09 mmol) and triethylamine (1.5 mL, 8.5 mmol) were stirred in dioxane (10 mL) at 0C. A solution of 2,6- dichlorobenzoyl chloride (1.5 g, 7.17 mmol) in THF (5 mL) was added dropwise until the starting material was consumed. The reaction was filtered, and the resultant solid washed with dioxane (3 x 20 mL). The filtrates were combined and used directly in the next reaction. MS (ESI) m/z 315 (M + H)+. Expected mass from chemical formula C12H9N3O3: 314.12 Da

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; FERGUSON, Fleur, M.; DOCTOR, Zainab, M.; (0 pag.)WO2020/5807; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, 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 25700-12-3, HPLC of Formula: C8H7N3

To a solution of 3-(1H-pyrazol-1-yl)pyridine (5 g, 34.4 mmol) in acetonitrile (68.9 ml) was added N-bromosuccinimide (7.97 g, 44.8 mmol). The reaction mixture was stirred at ambient temperature for 3H. The reaction mixture was diluted with EtOAc and washed with H2O, the organics were dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 0-60% EtOAc in hexanes to afford 3-(4-bromo-1H-pyrazol-1-yl)pyridine as a tan solid (6.99 g, 91%): mp 126-127 C.; 1H NMR (400 MHz, acetone-d6) delta 9.12 (d, J=2.5 Hz, 1H), 8.64 (d, J=0.5 Hz, 1H), 8.58 (dd, J=4.7, 1.4 Hz, 1H), 8.23 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.85 (s, 1H), 7.56 (ddd, J=8.3, 4.7, 0.7 Hz, 1H); EIMS m/z 223.

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

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 18213-75-7,Some common heterocyclic compound, 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, molecular formula is C5H8N4O, 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 5-amino-1-methyl-1H-pyrazole-4-carboxamide (0.200 g, 1.4 mmol) in ethanol (10 mL) were added ethyl 2,2,2-trifluoroacetate (0.123 g, 8.6 mmol) and sodium hydride (60% suspension in mineral oil, 0.571 g, 14.8 mmol) with stirring at 25 C. The reaction solution was degassed with nitrogen for 3 times and stirred at 90 C for 16 h. The resulting mixture was cooled toroom temperature and concentrated under reduced pressure. The residue was partitioned between aqueous hydrochloride acid (iN, 10 mL) and ethyl acetate (20 mL). The separated aqueous layer was extracted with ethyl acetate (2 x 15 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous sodium sulfate. The solids were filtered out and the filtrate was concentrated under vacuum. The title compound was obtained as a solid and used in next stepdirectly without further purification. MS (+ESI) m/z = 219.0.

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-methyl-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FORSTER, Ashley; CHEN, Yili; DWYER, Michael, P.; BERGER, Richard; WANG, Ming; NANDA, Kausik K.; BUNDA, Jaime L.; SHIPE, William D.; (100 pag.)WO2016/209749; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82560-12-1, 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step j04: 3-Tert-butyl-1H-pyrazol-5-amine (J-III) (1 eq., 40 g) was dissolved in dilute HCl (120 ml of HCl in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0-5 C. over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2CO3. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 C. After complete reaction, the reaction mixture was extracted with EE (3×500 ml), the combined organic phases were dried over sodium sulfate and the solvent was removed under vacuum. The purification (SiO2, 20% EE/hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15.1% 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, 3-Amino-5-tert-butylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; US2012/115893; (2012); 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. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 181585-93-3

To a solution of 2-methyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester and 1-methyl-5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.18 g, 6.37 mmo 1) in tetrahydro furan (20 mL) at 0C was added a lithium aluminum hydride solution (1 .OM in tetrahydrofuran, 7.65 mL, 7.65 mmol) drop wise. The resulting mixture was stirred at 0C for 20 min. To this solution was added ethyl acetate (1 mL) followed by few crystals of sodium sulphate decahydrate. The resulting mixture was stirred for 30 min then filtered, the filter cake washed with ethyl acetate and the filtrate evaporated. The residue was purified by flash chromatography (silica gel, 80 g, 50% to 70% ethyl acetate in hexanes) to give 1-methyl-3-nitro-1H-pyrazol-5-yl)methanol (496 mg, 50%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (s, 3 H) 4.53 (d, J=5.67 Hz, 2 H) 5.55 (t, J=5.48 Hz, 1 H) 6.93 (s, 1 H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BROTHERTON-PLEISS, Christine; JAIME-FIGUEROA, Saul; LOPEZ-TAPIA, Francisco Javier; LOU, Yan; OWENS, Timothy D.; WO2013/24078; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1613191-73-3, The chemical industry reduces the impact on the environment during synthesis 1613191-73-3, name is Allyl 3,5-diamino-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Step 2: 3-allyl 7-tert-butyl 2-amino-5, 6-dihydropyrazolo[l,5-a]pyrido[4,3-d]pyrimidine- 3, 7(8H)-dicarboxylate 4. [00239] A mixture of tert-butyl 3-(l,3-dioxolan-2-yl)-4-oxo-piperidine-l-carboxylate (100 mg, 0.3686 mmol), allyl 3,5-diamino-lH-pyrazole-4-carboxylate (67.15 mg, 0.369 mmol), KOH (5 mg, 0.0891 mmol) in dioxane (2 mL) was stirred at ambient temperature for 18h. The solid that formed was filtered and triturated in Et20 to afford compound 4 as a beige solid (lOOmg, 73%). LC-MS (M+H)+ 334.2; NMR (500 MHz, DMSO-d6) delta 8.85 (s, 1H), 6.37 (s, 2H), 6.00-6.07 (m, 1H), 5.51-5.55 (d, 1H), 5.23-5.26 (m, 1H), 4.75-4.76 (m, 2H), 4.55 (s, 2H), 3.69 (m, 2H), 3.32 (s, 2H), 2.93-2.95 (m, 2H), 1.40 (s, 9H).

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, Allyl 3,5-diamino-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; WO2014/143240; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 3469-69-0, 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. 3469-69-0 name is 4-Iodopyrazole, 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.

4-Iodo-1H-pyrazole (5.0 g, 25.8 mmol) was dissolved in DMF (50 mL), and K2C03 (4.27 g, 30.9 mmol) was added followed by 1-(chloromethyl)-4-methoxybenzene (3.86 mL, 28.4 mrnol). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then poured into water and extracted with Et20, washed with brine, dried over sodium sulfate, filtered and concentrated to afford 4-iodo-i-(4-methoxybenzyl)-lH-pyrazole (8.3 g, 26.4 mmol, 103 % yield).

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

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); 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. 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 110860-60-1

9.2 g of the intermediate (b) obtained in the above-described Synthesis Example 1-1 is dissolved in a mixed solution of 55 mL of acetic acid and 37 mL of propionic acid at room temperature. The resulting solution is cooled with ice to an internal temperature of -3C, and a 40% by weight solution of nitrosylsulfuric acid in sulfuric acid is dropwise added thereto over 10 minutes at an internal temperature of -3C to 4C. After stirring the mixture at an internal temperature of 4C for 1 hour, 0.2 g of urea is added thereto. Thereafter, the mixture is cooled to an internal temperature of-3C, followed by stirring for further 10 minutes to obtain a diazonium salt solution. Separately, 10 g of the intermediate (d) obtained in the above-described Synthesis Example 1-1 is completely dissolved in 150 mL of acetone, and the solution is cooled to an internal temperature of 17C and added to the above-described diazonium salt solution over 25 minutes at an internal temperature ranging from -3C to 3C. After completion of the addition, the mixture is stirred at 3C for 30 minutes, and the ice bath is removed to allow the temperature of the mixture to rise to room temperature over 30 minutes. After stirring the mixture at room temperature for 30 minutes, crystals obtained are collected by filtration, spray washed with 150 mL of acetone, then with 100 mL of water. Crystals obtained are suspended in 400 mL of water without drying, and a 8N potassium hydroxide aqueous solution is added thereto to adjust the pH to 5.7. After stirring the mixture at room temperature for 25 minutes, crystals obtained are collected by filtration, sufficiently spray washed with water. The thus-obtained crude pigment (1)-1 is dried at room temperature for 12 hours. The thus-obtained crude pigment (1-I) is suspended in a mixed solvent of 580 mL of acetone and 1160 mL of water, followed by stirring for 30 minutes under reflux. Thereafter, the mixture is cooled to room temperature over 10 minutes, followed by stirring at room temperature for 5 hours to obtain 17,6 g of beta-type crystal form azo pigment (1)-1 having the crystal form of the invention and represented by formula (1). Yield: 91.0% Visual observation of the thus-obtained beta-type crystal form azo pigment (1)-1 with a transmission microscope (manufactured by JEOL Ltd.; JEM-1010; electron microscope) reveals that the length of the long axis of primary particles is about 150 nm. When X-ray diffraction of the beta-type crystal form azo pigment (1)-1 is measured under the aforesaid conditions, characteristic X-ray peaks are shown at Bragg angles (2theta+/-0.2) of 7.0, 26.4, and 27.3. The X-ray diffraction pattern with characteristic Cu Kalpha line is shown in Fig. 10.

The synthetic route of 110860-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; EP2343343; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 26621-44-3, name is 3-Nitro-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 26621-44-3, Formula: C3H3N3O2

To a solution of compound 1 (25.0 g, 0.22 mol, 1.0 eq) in THF (250 mL) under Ar protection was added NaH (60%, 9.7 g, 0.24 mol, 1.1 eq) in portions.After stirring at room temperature for 10 min, SEMCl (44.2 g, 0.27 mol, 1.2 eq) was added dropwise.Stir overnight at room temperature.The reaction was quenched with saturated aqueous NH4Cl.The reaction solution was diluted with EtOAc, washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure.Purification by column (PE / EtOAc = 5/1) gave compound 2 (36.3 g, 67%) as a white solid.

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

Reference:
Patent; Longtaishen Pharmaceutical (Nanjing) Co., Ltd.; Yang Lei; (45 pag.)CN110590747; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

2458-26-6, name is 3-Phenyl-1H-pyrazole, 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 C9H8N2

General procedure: Methyl 3-(3-phenyl- 1 H -pyrazol- 1 -yljpropanoate Synthesised using the general procedure for Michael addition. General Synthetic Procedures and Characterisation Michael Addition 3-Phenyl-1 H-pyrazole (1 .73 mmol), acrylate (5.20 mmol) and DBU (130 muIota, 0.87 mmol) were combined in acetonitrile (3.5 ml), under nitrogen. The reaction was stirred at 50 C for 18 h and monitored by TLC. Once complete all of the volatiles were removed in vacuo and the crude material was purified by column chromatography, eluting with 15-25% ethyl acetate/petroleum spirits to obtain the desired product. Methyl 3-(3-phenyl- 1 H -pyrazol- 1 -yljpropanoate Synthesised using the general procedure for Michael addition.

The synthetic route of 2458-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MONASH UNIVERSITY; THE UNIVERSITY OF WESTERN AUSTRALIA; BAELL, Jonathan; PIGGOTT, Matthew; RUSSELL, Stephanie; TOYNTON, Arthur; RAHMANI, Raphael; FERRINS, Lori; NGUYEN, Nghi; (178 pag.)WO2015/172196; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics