Category: pyrazoles-derivatives

Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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. Recommanded Product: 3-Methylpyrazole

General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999percent purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98percent purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1453-58-3, its application will become more common.

Reference:
Article; Teo, Yong-Chua; Yong, Fui-Fong; Lim, Gina Shiyun; Tetrahedron Letters; vol. 52; 52; (2011); p. 7171 – 7174;,
Pyrazole – Wikipedia,
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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. 360056-45-7, name is Methyl 4-amino-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 360056-45-7

Reference Example 10 4-amino-N-methyl-1H-pyrazole-3-carboxamide A mixture of methyl 4-amino-1H-pyrazole-3-carboxylate obtained in Reference Example 2 (5.39 g, 38.2 mmol) and 40% methylamine/methanol solution (25 mL) was stirred at room temperature for 2 days. The mixture was concentrated under reduced pressure. Then methanol was added to the residue, and the mixture was concentrated under reduced pressure, the operation was twice repeated. Methanol and activated carbon (4.5 g) were added to the residue. After filtration, the solvent was evaporated under reduced pressure to give the title compound (5.31 g, yield 99%). 1H-NMR (DMSO-d6, 200 MHz): delta 2.71 (3H, d, J=4.8 Hz), 4.58 (2H, brs), 7.09 (1H, s), 7.72-7.86 (1H, brm).

The synthetic route of 360056-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
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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. 28466-26-4, name is 4-Aminopyrazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Aminopyrazole

1/-/-Pyrazol-4-amine (for a preparation see intermediate 1 ; 0.54 g, 6.5 mmol) was dissolved in acetonitrile (25 ml) with triethylamine (1.81 ml, 13.0 mmol) to give a red- purple suspension which was cooled in an ice-water bath. To the suspension was added a solution of 2,6-difluorobenzoyl chloride (Aldrich; 0.817 ml, 6.5 mmol) in acetonitrile (25 ml) dropwise over 15 min. The mixture was stirred cold under nitrogen. The reaction was stirred and allowed to warm slowly towards room temperature over 2 h, then at room temperature for 30 min. The reaction mixture was partitioned between EtOAc and water (-100 ml each). The aqueous phase was extracted with further EtOAc (2 x 50 ml). The combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue (1.41 g) was purified on silica (50 g) using 0-100% EtOAc-cyclohexane then 0-20% methanol- EtOAc. Relevant fractions were concentrated in vacuo to give some pure product (0.925 g) and some less pure material (0.50 g). The latter material was re-purified on silica (20 g) using EtOAc to give further pure product (0.366 g). The two batches of pure product were combined to give the title compound (1.28 g) as a pale cream solid; LCMS (System 1): MH+= 224, tRET = 2.08 min.

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; GLAXO GROUP LIMITED; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; WO2012/52459; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, 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 37687-24-4, COA of Formula: C9H12N2O4

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (2.00 g, 9.42 mmol), 2-bromo-1-(3,4-dihydro-2/-/-chromen-2-yl)ethanone (Intermediate 209A, 2.52 g, 9.90 mmol) and potassium carbonate (1.43 g, 10.4 mmol) in dry acetone (50 ml) was stirred at RT overnight. After filtering off the solids, the filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic phase was washed with water and brine, then dried over sodium sulfate and concen- trated. The residue was purified by flash-chromatography on silica gel (80 g, eluent: 0-25% ethyl acetate in petroleum ether) to give the title compound (2.88 g, 79% of theory). 1H-NMR (300 MHz, CDCIs): d [ppm] = 7.44 (s, 1H), 7.21-7.16 (m, 1H), 7.12-7.10 (m, 1H), 6.95- 6.90 (m, 2H), 5.95 (d, 1H), 5.69 (d, 1H), 4.75-4.71 (m, 1H), 4.42 (q, 2H), 4.30 (q, 2H), 2.88-2.82 (m, 2H), 2.36-2.17 (m, 2H), 1.40 (t, 3H), 1.35 (t, 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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; MUeLLER, Steffen; SCHOHE-LOOP, Rudolf; ORTEGA, HERNANDEZ, Nuria; SUeSSMEIER, Frank; JIMENEZ NUNEZ, Eloisa; BRUMBY, Thomas; LINDNER, Niels; GERDES, Christoph; POOK, Elisabeth; BUCHMUeLLER, Anja; GAUGAZ, Fabienne, Zdenka; LANG, Dieter; ZIMMERMANN, Stefanie; EHRMANN, Alexander, Helmut, Michael; GERISCH, Michael; LEHMANN, Lutz; TIMMERMANN, Andreas; SCHAeFER, Martina; SCHMIDT, Georg; SCHLEMMER, Karl-Heinz; FOLLMANN, Markus; KERSTEN, Elisabeth; WANG, Vivian; GAO, Xiang; WANG, Yafeng; (801 pag.)WO2019/219517; (2019); A1;,
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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. 23170-45-8, name is Methyl 3-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 23170-45-8

General procedure: Compound (11a-g or 12f-g) (1.2 mmol), CuI (19.1 mg, 0.1 mmol), trans-N,N’-dimethyl-1,2-cyclohexane-diamine (29 mg, 0.2 mmol), K2CO3 (0.29 g, 2.1 mmol) and DMF (3 mL) were added to a tube filled with argon. The mixture was stirred at 110 C for 24 h. The reaction was diluted with H2O (20 mL) and extracted with EtOAc (15 mL x 2). The combined organic phases were washed with H2O (20 mL x 2) and brine (30 mL), dried over MgSO4 and concentratedin a vacuum. The residue was purified by flash column chromatography (12-25% EtOAc in petroleum ether).

According to the analysis of related databases, 23170-45-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jing; Wu, Fangping; Liu, Xingguo; Zou, Yake; Chen, Huixiong; Li, Zheng; Zhang, Lei; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 20 – 30;,
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Synthetic Route of 1124-16-9, These common heterocyclic compound, 1124-16-9, name is 5-Amino-1-isopropyl-3-methylpyrazole, 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.

2-[(5-Chloro-2-{[3-methyl- 1 -(1 -methylethyl)- 1 H-pyrazol-5-yllami no)-4-pyridi nyl)aminol-N( methyloxy)benzamideA microwave tube was charged with 2-[(2,5-dichloro-4-pyridinyl)amino]-N- (methyloxy)benzamide (70 mg, 0.224 mmol), {3-methyl-1-(1-methylethyl)-1H-pyrazol-5- amine (70 mg, 0.503 mmol) and cesium carbonate (230 mg, 0.706 mmol). The reactionmixture was degassed with nitrogen for 10 mm. At same time, BINAP (50 mg, 0.080 mmol) and palladium(ll) acetate (10 mg, 0.045 mmol) were added. The reaction mixture was heated in a microwave at 160 C for 40 mm. The crude material was purified on reverse-phase HPLC (Gilson) eluting with CH3CNH20 with 0.1% formic acid which gave a title compound (15mg, 15%); MS: M(C20H23C1N602) = 414.89, (M+H) = 415, 416; 1H NMR(400 MHz, CHLOROFORM-d) 6 ppm 9.42 (br. s., 1 H) 8.71 (br. s., 1 H) 8.02 (s, 1 H) 7.54 (br. s., 1H) 7.06 (t, J=7.5 Hz, 1 H) 6.48 (s, 1 H) 6.32 (br. s., 1 H) 5.86 (s, 1 H) 4.47 (dt, J=13.4, 6.7 Hz, 1 H) 3.92 (s, 3 H) 2.26 (s, 3 H) 1.41 – 1.43 (d, J = 6.6 Hz, 2H).

The synthetic route of 1124-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; AUGER, Kurt, R.; DAR, Mohammed, M.; FLEMING, Ronald, A.; WO2013/3575; (2013); 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. 113402-89-4, name is 3-Methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H7N3

4-Bromo-6,7-dimethoxycinnoline (530 mg, 2.0 mmol), 5-methyl-4H-pyrazol-3-amine (150 mg, 1.5 mmol), toluene (4 mL), tris(dibenzylideneacetone)dipalladium(0) (45 mg, 0.049 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthane (70.0 mg, 0.121 mmol) and sodium tert-butoxide (1.80E2 mg, 1.87 mmol) were combined in a 10 mL sealed tube. The reaction was irradiated in a microwave on 300 watts, at 140°C for 600 seconds The reaction mixture was then filtered through Celite using methanol and methylene chloride and subsequently concentrated. The crude product was then dissolved in 1 mL methanol and filtered through a Gelman Acrodisk 0.45 micron HPLC filter. Purification using a C18 column preparative (30 x 00 mm) HPLC column and a gradient of 20-80percent acetonitrile:water (with 0.1percent formic acid) and a flow rate of 45 mL/min afforded 40.9mg (8percent) of 6,7-dimethoxy-N-(5-methyl-4H-pyrazol-3-yl)cinnolin-4-amine hydroformate as a yellow solid. MS [M+H] = 286.1, LC/MS (EI) tR 3.14 min (Method B), .H NMR (DMS0-d6) 8 (ppm) d 12.57 (s, 1 H), 9.38 (s, 1 H), 7.94 (s, 1 H), 6.12 (s, 1.5 H), 5.75 (s, 0.5 H), 4.01 (s, 3 H), 4.00 (s, 3 H), 2.30 (s, 3 H)

The synthetic route of 113402-89-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/28957; (2006); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 75415-03-1, 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. 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 4a (2 mmol), NaH (2.4 mmol) and indole were dissolved in DMF (10 mL). The reaction mixture was stirred at room temperature for 12h before diluted with water (20 mL) and extracted with ethyl acetate (30 mL × 3). The organic layer was concentrated in vacuum. Purication by ash column chromatography gave the target product 5h.

The chemical industry reduces the impact on the environment during synthesis 2-(1H-Pyrazol-3-yl)pyridine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Chen-Ru; Wang, Ze-Feng; Shi, Lu; Wang, Zhong-Chang; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2382 – 2390;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 139756-02-8, 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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Chloronicotinic acid (250 mg, 1.587 mmol), 4-amino-1-methyl-3-n-propyl-5-pyrazole-carboxamide (290 mg, 1.589 mmol, 1.0 equiv), PyBrOP (820 mg, 1.759 mmol, 1.1 equiv) and Et3N (0.440 mL, 3.160 mmol, 2.0 equiv) in DCE (5 mL) were heated using microwave irradiation for 20 min at 120 C. The reaction mixture was reduced in vacuo and purified via column chromatography (7.5 % MeOH in EtOAc) to give the title compound (509 mg, 100%) as an off white solid. 1H NMR (400 MHz, CDCl3)1 delta 8.57 (dd, J=4.8 Hz, J = 1.8 Hz , 1H), 8.22 (dd, J=7.8 Hz, J = 1.8 Hz, 1H), 7.90 (br s, 1H), 7.45 (dd, J=7.8 Hz, J = 4.8 Hz, 1H), ~7.26 (1H), 4.06 (s, 3H), 3.49 (d, J=4.4 Hz, 1H), 2.59 (t, J=7.6 Hz, 2H), 1.67 (sxt, J=7.6 Hz, 2H), 0.97 (t, J=7.6 Hz, 3H). 13C NMR (100 MHz, CDCl3) 166.1, 161.4, 151.8, 147.5, 147.1, 140.0, 132.9, 130.1, 123.0, 114.2, 39.2, 27.8, 22.4, 13.9. LCMS (C18): tR (min) = 0.98, (ESI) found 665.1 [2M + H]+. HRMS: C14H16ClN5O2 requires 322.1065 [M + H+]; Found.

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, 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Cuihua; Ashton, Trent D.; Gustafson, Alden; Bland, Nicholas D.; Ochiana, Stefan O.; Campbell, Robert K.; Pollastri, Michael P.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2579 – 2581;,
Pyrazole – Wikipedia,
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Application of 51516-67-7, 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. 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Intermediate 4 (1mmol) and the intermediate 7 (1mmol) were dissolved in ethanol to the glass flask, then HCl solution was added as a catalyst refluxed at 80C for 15-18h. After the TLC monitoring reaction was completed, the mixture was vacuum filtered and concentrated. Finally, the above crude product can be isolated and purified by column chromatography (Hexane/EtOAc=8:1) to obtain target compounds.

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-chlorophenyl)-1H-pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cao, Hai-Qun; Chu, Zhi-Wen; Liu, Hao; Lv, Xian-Hai; Xia, Dong-Guo; Bioorganic Chemistry; vol. 99; (2020);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics