Tag: M.W=0-100

Application of 132712-71-1, 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 132712-71-1 as follows.

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95%, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol %) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

According to the analysis of related databases, 132712-71-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31108-57-3,Some common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, molecular formula is C4H3N3, 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 I-BA10 (20 mg, 0.047 mmol) in acetone (2 mL) were added K2C03 (13 mg, 0.1 mmol) and lH-pyrazole-4-carbonitrile (9 mg, 0.1 mmol) at l5C. The reaction mixture was stirred for lh at l5C. The reaction mixture was filtered and the mother liquor was concentrated. The residue was purified by flash column (0-30% of EtOAc in PE) to give I- BA11 (10.3 mg, 50%) as a solid. (2459) The structure was confirmed by NOE. (2460) 1H NMR (400 MHz, CDCl3) dH 7.86 (s, 1H), 7.81 (s, 1H), 5.10-4.90 (m, 2H), 2.60 (d, J= 8.8 Hz, 1H), 2.00-1.58 (m, 12H), 1.51-1.28 (m, 11H), 1.26 (s, 3H), 1.24-1.12 (m, 2H), 1.10 (s, 3H), 1.08-0.85 (m, 3H); MS ESI calcd. for C27H38N30 [M+H-H20]+ 420, found 420

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (646 pag.)WO2019/126761; (2019); 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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Methylpyrazole

A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 °C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 °C. The reaction mixture was stirred for 1 h at 70 °C, and then a second portion of potassium permanganate (111 g) was added at 70 °C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 °C. The reaction mixture was stirred a further 2 h at 70 °C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 mL. The aqueous was chilled to 0 °C, acidified with concentrated HC1, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57percent). Dimethyl sulfate (236 g, 177 ML, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20percent aqueous sodium hydroxide (850 ML) at 40 °C. The reaction mixture was heated at 80 °C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HC1, the precipitate filtered, washed with water, and dried under vacuum to yield 1-METHYLPYRAZOLE-5-CARBOXYLIC acid (85 g, 38percent). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid. A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 ML) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension of Pd-C (10 wtpercent, 9.3 g) in toluene (500 ML), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63percent) as a low melting white solid (bp = 92 °C COMMAT; 8 MMHG).

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; MERCK & CO., INC.; WO2004/58763; (2004); 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. 81945-73-5, name is 1H-Pyrazol-1-ol, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 81945-73-5

1-Benzyloxy-lH-pyrazole; To a mixture of pyrazol-1-ol (1 g, 11.9 mmol) and /-Pr2NEt (2.02 mL, 11.9 mL) in DCM (15 mL) at 0 0C was added BnBr (4.09 mL, 23.8 mmol). The mixture was allowed to warm up to r.t. and stirred at this temperature for 22 h. The mixture was concentrated in vacuo to afford a yellow paste. The crude product was purified by flash chromatography (silica gel, hexanes/DCM/Et2O (100:0:0 to 80:10:10), Rf 0.23 in hexanes/DCM/Et2O (34:3:3)) to provide the title product as a yellow oil (1.17 g, 56%).

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 81945-73-5.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37599-58-9, name is (1H-Pyrazol-3-yl)methanamine, 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 37599-58-9, Recommanded Product: (1H-Pyrazol-3-yl)methanamine

To a solution of 4-chloro-7-(l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazol-5- yl)quinolin-2-amine (20 mg, 0.061 mmol) and (lH-pyrazol-3-yl)methanamine (59.1 mg, 0.608 mmol) in DMSO (0.5 mL) was added Hunig’s Base (0.032 mL, 0.182 mmol). The reaction was heated to 120 C overnight. The reaction was cooled, diluted with water, and extracted three times with EtOAc. The organic layers were concentrated, then dissolved in 0.4 mL DCM and 0.4 mL TFA. After 1 hour, the reaction was complete by LCMS. The reaction was concentrated and azeotroped with DCM. The residue was dissolved in DMF, filtered through a syringe filter, and the crude material was purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 200 mm x 19 mm, 5-muiotatauiota particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1%trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: a 0-minute hold at 0% B, 0-40% B over 20 minutes, then a 4-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation. The material was further purified via preparative LC/MS with the following conditions: Column: XBridge C18, 200 mm x 19 mm, 5-mupiiota particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: a 3- minute hold at 0% B, 0-32% B over 25 minutes, then a 5-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation to give N4-((lH-pyrazol-3-yl)methyl)-7-(lH-pyrazol-5-yl)quinoline-2,4- diamine (4.6 mg, 24.7%). NMR (500 MHz, DMSO-de) delta 8.00 (br d, J=8.2 Hz, 1H),7.75 (s, 1H), 7.72 (br s, 1H), 7.58 (br s, 1H), 7.54 (br d, J=7.9 Hz, 1H), 7.43 (br s, 1H),6.76 (s, 1H), 6.62 – 6.41 (m, 1H), 6.20 (s, 1H), 5.76 (s, 1H), 4.42 (br d, J=5.2 Hz, 2H). LC RT: 0.99 min. M/Z= 306.18. (1550)

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; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0, The chemical industry reduces the impact on the environment during synthesis 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 1-methyl-1H-pyrazol-3-amine 58 (5.0 g, 51.50 mmol) in Conc.HC1 (40 mL) at 0°C, sodium nitrite (5.30 g, 77 mmol) in water was added at 0°C and the mixture was stirred at RT for 30 mm. Copper (I) chloride was dissolved in concentrated hydrochloric acid (10 mL) and added to the above mixture drop-wise. The reaction was heated at 60°C, catalytic amount of Cu(I)Cl was added at 60°C (initiating the evolution of gas). Reaction mixture was stirred at 60°C for 30 mm. The mixture was then poured to chilled 50percent NaOH solution & stirred properly; aqueous was extracted with DCM. The organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered and solvents evaporated to obtain a crude product (5.50 g, quantitative yield). 1HNMR (400 MHz, CDC13): oe 7.27 (d, 1H), 6.15 (d, 1H), 3.85 (s, 3H).

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-Methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); 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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H4N2

At room temperature, pyrazole (0.2 mol) was dissolved in concentrated sulfuric acid (50 mL) and slowly raised to a temperature of 60 CConcentrated nitric acid (9.2 mL) was added and stirring was continued at 60 C for 1.5 hours.After completion of the reaction, the reaction solution was poured into 600 g of ice water, and the resulting white solid was separated by filtration and washed with water.After extraction with ethyl acetate (100 mL x 3), the organic phase was washed successively with 1% sodium bicarbonate solution (100 mL), water (100 mL) and physiological saline (100 mL), dried over anhydrous sodium sulfate and filtered, Finally, the organic phase liquid was rotary evaporated to give a white solid which was combined with the previously obtained white solid to give compound 2a. The resulting compound 2a (12 mmol) was dissolved in DMSO (9 mL)And potassium carbonate (10.9 mmol) was added successively thereto,Methyl iodide (6 mmol),8-hydroxyquinoline (1 mmol),CuI (0.58 mmol). Argon under the conditions of protection, stirMixed and heated to 130 C,After 20 hours of reaction,The reaction solution was poured into an appropriate amount of water,The resulting green solid was separated by filtration.The mother liquor was extracted with ethyl acetate (100 mL x 3). Finally, the organic phase liquid was evaporated to dryness and the resulting crude product was combined with the previously obtained green solid and purified by silica gel column chromatography to obtain Compound 4a. Compound 4a (1 mmol), hydrazine hydrate (0.5 mL) was added to ethanol (1 mL) and palladium on carbon (0.02 g) was added as catalyst.Heated at 80 C and refluxed for 10 minutes. After the completion of the reaction, the resulting mother liquor was subjected to rotary evaporation and drying to obtain Compound 5a. Compound 4a (1 mmol), hydrazine hydrate (0.5 mL) was added to ethanol (1 mL) and palladium on carbon (0.02 g) was added as catalyst.Heated at 80 C and refluxed for 10 minutes. After the completion of the reaction, the resulting mother liquor was subjected to rotary evaporation and drying to obtain Compound 5a. The compound 8a (1 mmol),EDC (1 mmol), HOBt (1 mmol) was added to DMF(3 mL) for 30 min.The compound 5a, DMAP (1 mmol), triethylamine (500 [mu] L) were added to the activated DMFSolution. At room temperature, stir overnight.After completion of the reaction, 100 mL of saturated sodium chloride solution was added to the reaction solution, and the mixture was washed with ethyl acetateEster extraction (200 mL x 3) extraction. Finally, the organic phase liquid was evaporated under vacuum and evaporated to dryness to obtain a crude product, using a silica gel columnSeparation and purification to give the final compound 9a to give a white solid powder in a yield of 86.4%

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; Nanjing University; Zhu Hailiang; Shi Lu; Wang Zefeng; Wang Chenru; (14 pag.)CN107098861; (2017); A;,
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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H7N3

3rd generation BrettPhos pre-catalyst (0.227 g, 0.25 mmol) was added to methyl i-(i((tert-butoxycarbonyl)amino)-3 -methoxypropan-2-yl)-4-(2-chloro-5 -methylpyrimidin-4- yl)-1H-pyrrole-2-carboxylate (1.1 g, 2.51 mmol), i-methyl-1H-pyrazol-5-amine (0.487 g, 5.01 mmol) and cesium carbonate (2.041 g, 6.27 mmol) in 1,4-dioxane (30 mL) at 25 °C under nitrogen. The resulting solution was stirred at 85 °C for 3 hours. The reactionmixture was poured into water (25 mL), extracted with EtOAc (3 x 50 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford crude yellow solid. The crude product was purified by flash silica chromatography, elution gradient 80 to 90percent EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford methyl 1 -(1- ((tert-butoxycarbonyl)amino)-3 -methoxypropan-2-yl)-4-(5 -methyl-2-(( i-methyl-i H25 pyrazol-5-yl)amino)pyrimidin-4-yl)-1H-pyrrole-2-carboxylate (0.700 g, 55.9 percent) as a whitefoam. mlz: ES+ [M+H]+ 500.

The synthetic route of 1192-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3920-50-1, A common heterocyclic compound, 3920-50-1, name is Pyrazole-3-carboxaldehyde, molecular formula is C4H4N2O, 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 flask was charged with CuI (79 mg, 0.42 mmol), 8-hydroxyquinoline-N-oxide (134 mg, 0.83 mmol), Cs2CO3 (2.713 g, 8.33 mmol), 1H-pyrazole-3-carbaldehyde 42 (400 mg, 4.16 mmol). The flask was evacuated and backfilled with argon. Iodobenzene (0.70 mL, 6.24 mmol) and DMSO (5 mL) were added to the flask under argon atmosphere. After stirring at 90 C for 48 h, the mixture was diluted with water, and extracted with ethyl acetate (3 x 30 mL). The combined organic phases were washed with brine, dried with Na2SO4, filtered, concentrated and purified by silica gel chromatography to afford 68b as a pale yellow solid (329 mg, 46 %).

The synthetic route of 3920-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yao, Yiwu; Liao, Chenzhong; Li, Zheng; Wang, Zhen; Sun, Qiao; Liu, Chunping; Yang, Yang; Tu, Zhengchao; Jiang, Sheng; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 639 – 652;,
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. 35277-02-2, name is 4-Fluoro-1H-pyrazole, A new synthetic method of this compound is introduced below., Formula: C3H3FN2

2-Chloro-N-[(dimethylamino)methylene]-5-[(diphenylmethylene)amino]pyridine-3-sulfon- amide (1.00 g, 2.34 mmol) was dissolved in DMSO (18 mL). 4-Fluoro-1H-pyrazole (403mg, 4.69 mmol), potassium iodide (389 mg, 2.34 mmol) and potassium phosphate (746 mg, 3.51 mmol) were added and the reaction mixture was stirred overnight at 100CC. Afterwards it was concentrated in vacuo, extracted with dichloromethane/water and the organic phase was washed with brine and dried over sodium sulfate followed by concentration in vacuo.Due to partial deprotection, the material was redissolved in dimethylformamide (2 mL) and stirred overnight with 1 ,1-dimethoxy-N,N-dimethylmethanamine (0.5 mL). The reaction mixture was concentrated in vacuo, extracted with dichloromethane/water and the organic phase was washed with brine and dried over sodium sulfate followed by concentration invacuo to give crude N-[(dimethylamino)methylene]-5-[(diphenylmethylene)amino]-2-(4-fluoro-1 H-pyrazol-1 -yl)pyridine-3-sulfonamide (723 mg).LC-MS (Method A): Rt = 1.25 mm, MS (ESIpos): m/z = 477 [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; 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