Day: June 18, 2021

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. 55864-87-4, name is Ethyl 4-nitro-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 55864-87-4

a) Ethyl 4-NITRO-LH-PYRAZOLE-3-CARBOXYLATE (741 mg, 4 mmol) was heated at 90C with a concentrated solution of aqueous ammonia (28%, 20 ML) in a sealed vessel for 3 hours. The mixture was evaporated and the residue was triturated with diethyl ether to give 4-NITRO-LH- pyrazole-3-carboxamide (0.54 g, 86% yield) as a white solid: 1H-NMR (DMSO d6) : 8. 70 (s, 1H), 8.06 (s, 1H), 7. 83 (s, 1H); MS (+VEESI) : 157.13 (M+H) +.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/94410; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

63874-95-3, name is 1-Benzyl-1H-pyrazole-4-carbaldehyde, 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. Recommanded Product: 63874-95-3

General procedure: Step 7. Preparation of (S)-5-chloro-4-((1-((6-(difluoromethyl)-3-fluoropyridin-2- yl)methyl)pyrrolidin-3-yl)(methyl)amino)-2-fluoro-//-(thiazol-4- yl)benzenesulfonamide formate To a solution of (S)-5-chloro-2-fluoro-4-(methyl(pyrrolidin-3-yl)amino)-//- (thiazol-4-yl)benzenesulfonamide (0.100 g, 0.234 mmol) and 6-(difluoromethyl)-3- fluoropicolinaldehyde (0.102 g, 0.585 mmol) in dichloromethane (5 ml_) was added acetic acid (0.50 ml_) and sodium triacetoxyborohydride (0.148 g, 0.702 mmol) portionwise and the resulting mixture was stirred at ambient temperature for 1 h. Concentration in vacuo and purification of the residue by preparative reverse phase HPLC, using acetonitrile in water containing 0.225% formic acid as eluent, afforded the title compound as a colorless solid (0.017 g, 13% yield): H NMR (400 MHz, CD3OD) delta 8.74 (d, J = 2.2 Hz, 1 H), 8.40 (br s, 0.8H), 7.83-7.71 (m, 3H), 7.04 (d, J = 2.2 Hz, 1 H), 7.00 (d, J = 12.0 Hz, 1 H), 6.75 (t, J = 55.2 Hz, 1 H), 4.35-4.26 (m, 1 H), 4.16-4.02 (m, 2H), 3.09-2.96 (m, 3H), 2.92-2.84 (m, 1 H), 2.83 (s, 3H), 2.22-2.12 (m, 1 H), 2.05-1.92 (m, 1 H), NH and COOH not observed; MS (ES+) m/z 549.9 (M + 1), 551.9 (M + 1).

The synthetic route of 63874-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BURFORD, Kristen, Nicole; CHOWDHURY, Sultan; COHEN, Charles, Jay; DEHNHARDT, Christoph, Martin; DEVITA, Robert, Joseph; EMPFIELD, James, Roy; FOCKEN, Thilo; GRIMWOOD, Michael, Edward; HASAN, Syed, Abid; JOHNSON, James, Philip, Jr.; ZENOVA, Alla, Yurevna; (493 pag.)WO2017/201468; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31230-17-8,Some common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

70A. 2-Chloro-N-(5-methyl-1H-pyrazol-3-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine This was prepared from 1B and 5-methyl-1H-pyrazol-3-amine as described for 1C: MS: 249 (M+H)+; HPLC Ret Time: 2.04 min (Phenomenex-Luna S10 4.6*50 mm column, 3 min gradient, 4 mL/min).

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

Reference:
Patent; Bristol-Myers Squibb Company; US2008/9497; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 139756-02-8, These common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, 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: We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1).

Statistics shows that 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide is playing an increasingly important role. we look forward to future research findings about 139756-02-8.

Reference:
Article; Reddy, G. Lakshma; Guru, Santosh Kumar; Srinivas; Pathania, Anup Singh; Mahajan, Priya; Nargotra, Amit; Bhushan, Shashi; Vishwakarma, Ram A.; Sawant, Sanghapal D.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 201 – 208;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 51105-90-9 as follows. Formula: C5H6N2O2

General procedure: Sulfonamide A (e.g.1.29 mmol) was dissolved in acetonitrile (15 mL in case of 1.29 mmol scale) and finely powdered potassium carbonate (3.0 eq) and the corresponding azole(1.5 eq) were added. Stirring was continued at 100 – 110C until TLC showed consumption of starting material. The solvent was removed under reduced pressure, followed by addition of water and dichloromethane. Afterwards, the phases were separated, the organic phase was dried and it was concentrated in vacuo. The crude was either used without further purification or purified as indicated in the examples.

According to the analysis of related databases, 51105-90-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; CLEVE, Arwed; BRAeUER, Nico; HERBERT, Simon, Anthony; KOCH, Markus; DAHLLOeF, Henrik; OSMERS, Maren; HARDAKER, Elizabeth; LISHCHYNSKYI, Anton; (673 pag.)WO2017/191000; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O2, 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. Formula: C6H8N2O2

To a solution of 1-fluoro-4-iodo-benzene (1.47 g, 6.6 mmol, 1.3 eq) and ethyl 1H-pyrazole-3-carboxylate (0.71 g, 5.1 mmol, 1 eq) in 15 mL of toluene was added CuI (0.19 g, 1.0 mmol, 0.2 eq), trans-N,-N-dimethylcyclohexane 1,2-diamine (0.4 mL, 2.5 mmol, 0.2 eq), and potassium carbonate (1.4 g, 10 mmol, 2 eq). The reaction mixture was heated at 110° C. for 2 d then filtered and concentrated. The residue was purified by silica gel column chromatography (hex:EtoAc 4:1) to afford ethyl 1-(4-fluorophenyl)pyrazole-3-carboxylate (0.92 g, 3.9 mmol, 77percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5932-27-4, its application will become more common.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (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

A solution of methyl 1H-pyrazole-3-carboxylate (5 g) in dry acetonitrile was treated with cesium carbonate (32.3 g) and methyl iodide (6.45 g) and the mixture was stirred at rt for 2 h. The suspension was filtered and the volatiles were removed under reduced pressure. The residue was purified by chromatography (SiO2, Cy/EtOAc) to yield the desired product (66% yield). LC-MS (Method 1): m/z [M+H]+=141.2 (MW calc.=140.14); Rt=1.0 min.

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; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194443; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25016-16-4, These common heterocyclic compound, 25016-16-4, name is 1-(1H-Pyrazol-4-yl)ethanone, 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-bromo-5-fluoropyridine (4.1 g, 9.1 mmol), l -(lH-pyrazol-4- yl)ethanone (5, 1.6 g, 9.1 mmol) and Cs2C03(3.55 g, 10.9 mmol) in 15 mL of DMF was heated at 120 C in a microwave oven for 30 minutes. The reaction was cooled to room temperature and diluted with 150 mL of water and filtered. The solid was collected and dried to provide the desired compound (6, 2 g, 7.5 mmol, 83% yield).

Statistics shows that 1-(1H-Pyrazol-4-yl)ethanone is playing an increasingly important role. we look forward to future research findings about 25016-16-4.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; XU, Ying-Zi; ARTIS, Dean, R.; BOWERS, Simeon; HOM, Roy, K.; SHAM, Hing, L.; YUAN, Shendong; WO2013/142613; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1280210-79-8, The chemical industry reduces the impact on the environment during synthesis 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, I believe this compound will play a more active role in future production and life.

To a solution of tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (15.0 g, 71.8 mmol) in DMF (150 mL) was added NaH (60% in mineral oil) (8.6 g, 215.4 mmol) while the reaction mixture was cooled with an ice bath. When the addition was complete, the resulting mixture was allowed to warm to room temperature and was stirred at room temperature for 30 min. At this point, l-bromo-2- methoxyethane (19.8 g, 143.6 mmol) was added into the reaction mixture, and stirring was continued at room temperature for 2 h. The reaction mixture was then quenched with water (300 mL), and extracted with EtOAc (150 mL x 3). The combined organic layer was washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 122 and 122-A (19.0 g, 99%) as a colorless oil. MS 268.2 [M + H]+. [0072] Synthesis of 123 and 123-A. To a solution of 122 and 122-A (6.5 g, 24.3 mmol) in DCM (60 mL) cooled with an ice bath was added TFA (30 mL). The reaction mixture was stirred at room temperature for 1 h, whereupon the solvent was removed in vacuo to give 123 and 123-A as a crude product mixture which was used directly in the next step without further purification. MS 168.1 [M+H]+. (0114) [0073] Synthesis of 124 and 124-A. To a solution of 123 and 123-A (24.3 mmol, crude product from last step) and A4 (9.3 g, 20.3 mmol) in DMSO (200 mL) was added Na2C03 (21.5 g, 203 mmol), and the reaction mixture was stirred at room temperature for 4 h. The mixture was then diluted with water (400 mL) and extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 124 and 124-A (4.5 g, 50%) as a yellow solid. MS 411.0, 413.1 [M+H]+. (0115) [0074] Synthesis of 125 and 125- A . A mixture of 124 and 124-A (500 mg, 1.22 mmol), 5-chlorothiophen-2-ylboronic acid (237 mg, 1.46 mmol) and K2C03 (169 mg, 1.23 mmol) in dioxane/H20 (10 mL/2 mL) was treated with Pd(PPh3)4 (45 mg, 0.06 mmol) under a N2 atmosphere. The reaction mixture was stirred at 50 C for 3 h and then concentrated in vacuo. The residue was taken up in EtOAc (30 mL), and the resulting solution was washed with brine (10 mL x 3). The organic layer was then dried over anhydrous Na2S04 and concentrated in vacuo. The crude residue was purified by Prep-TLC (DCM : MeOH = 20: 1) to give a mixture of 125 and 125-A (450 mg, 82%) as a yellow solid. MS 449.2 [M + H]+. (0116) [0075] Synthesis of Compound 6 and Compound 6A. A mixture of 125 and 125-A (450 mg, 1.0 mmol) and Raney Ni (100 mg) in DCM/MeOH (6mL/6 mL) was stirred at room temperature for 1 h under a H2 atmosphere. Raney Ni was then removed by filtration through Celite, the filtrate was concentrated en vacuo, and the residue was purified by Prep-TLC (DCM : MeOH = 10 : 1). The mixture of regioisomers was then separated by using chiral HPLC (Column: Chiralcel OD-3; Solvent: MeOH; Flow rate: 2 mL/min; RTi843 = 3.477 min, RTi843A = 4.142 min) to give Compound 6 (99 mg, 24%) as a white solid (MS 419.2 (0117) [M+H]+) and Compound 6A (50 mg, 12%) as a white solid. MS 419.2 [M+H]+.

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, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RODIN THERAPEUTICS, INC; FULLER, Nathan, Oliver; LOWE, John, A.; (45 pag.)WO2019/32528; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 26621-44-3,Some common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, 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.

A solution of 3-nitro-1H-pyrazole (Intermediate 2, 205 mg, 1.81 mmol) in anhydrous N,N-dimethylformamide (3.5 mL) was treated with (R)-glycidol (148 mg, 2.00 mmol) and potassium carbonate (770 mg, 5.58 mmol). The mixture was heated in a sealed vial at 120 C. for 1 h. After this time, the mixture was diluted with water (15 mL) and extracted with ethyl acetate (6×25 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (15 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (Teledyne Isco RediSep Flash Column 40 g, 15-100% ethyl acetate/hexanes) afforded (S)-3-(3-nitro-pyrazol-1-yl)-propane-1,2-diol (118 mg, 34%) as a thick yellow oil. 1H-NMR (400 MHz, CD3OD) delta 3.55 (2H, d, J=5.2 Hz), 4.02-4.05 (1H, m), 4.20 (1H, dd, J=13.6 Hz, 7.6 Hz), 4.39 (1H, dd, J=14.0 Hz, 3.6 Hz), 6.92 (1H, d, J=2.0 Hz), 7.79 (1H, d, J=2.0 Hz).

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

Reference:
Patent; Berthel, Steven Joseph; Haynes, Nancy-Ellen; Kester, Robert Francis; McDermott, Lee Apostle; Qian, Yimin; Sarabu, Ramakanth; Scott, Nathan Robert; Tilley, Jefferson Wright; US2009/264434; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics