Category: pyrazoles-derivatives

Some common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. name: 1-Methyl-1H-pyrazole-4-sulfonyl chloride

General procedure: A mixture of the appropriate (aryloxy)ethyl piperidine(0.38 mmol) in CH2Cl2 (3 mL), and TEA (1.14 mmol) was cooled down (ice bath), and arylsulfonyl chloride (0.46 mmol) was added at 0 C in one portion. The reaction mixture was stirred for 2-6 h under cooling. Then, the solvent was evaporated and the sulfonamides were purified using silica gel column with CH2Cl2/MeOH as an eluting system. Free bases were then converted into the hydrochloride salts by treatment of their solution in anhydrous ethanol with 1.25 M HCl in MeOH.; 9.2.6.11 1-Methyl-N-{1-[2-(biphenyl-2-yloxy)ethyl]piperidin-4-yl}-N-methyl-1H-pyrazole-4-sulfonamide (20) Yellow oil, 100 mg following chromatographic purification over silica gel with CH2Cl2/MeOH (9:0.7); LC/MS purity 100%, tR = 4.65, C24H30N4O3S, MW 454.58, Monoisotopic Mass 454.20, [M+H]+ 455.5. 1H NMR (300 MHz, CDCl3) delta 1.40-1.48 (m, 2H), 1.62-1.65 (m, 2H), 2.05 (td, J = 11.90, 2.20 Hz, 2H), 2.66-2.70 (m, 2H), 2.71 (s, 3H), 2.83-2.90 (m, 2H), 3.68-3.80 (m, 1H), 3.94 (s, 3H), 4.04 (t, J = 5.63 Hz, 2H), 6.93-6.97 (m, 1H), 7.03 (td, J = 7.45, 1.06 Hz, 1H), 7.28-7.33 (m, 3H), 7.34-7.40 (m, 2H), 7.49-7.51 (m, 1H), 7.51-7.53 (m, 1H), 7.69 (d, J = 0.54 Hz, 1H), 7.73 (s, 1H). 13C NMR (75 MHz, CDCl3) delta 28.59, 29.19, 39.57, 53.35, 55.00, 56.78, 66.94, 112.70, 121.18, 122.22, 126.83, 127.79, 128.58, 129.61, 130.86, 131.13, 131.35, 138.17, 138.48, 155.63. Anal. calcd for C24H30N4O3S·HCl: C: 58.70, H: 6.36, N: 11.41, S: 6.53; Found C: 58.96, H: 6.49, N: 11.42, S: 6.88. Mp for C24H30N4O3S·HCl: 189.5-189.9 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288148-34-5, its application will become more common.

Reference:
Article; Canale, Vittorio; Kurczab, Rafa?; Partyka, Anna; Sata?a, Grzegorz; S?oczy?ska, Karolina; Kos, Tomasz; Jastrz?bska-Wi?sek, Magdalena; Siwek, Agata; P?kala, Elzbieta; Bojarski, Andrzej J.; Weso?owska, Anna; Popik, Piotr; Zajdel, Pawe?; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 130 – 139;,
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Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-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 2075-46-9, category: pyrazoles-derivatives

General procedure: A mixture of methyliodide (12 mmol), 1a (6 mmol) and K2CO3 (9 mmol) in DMF (6 mL) was stirred overnight at room temperature. Then the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (25 mL × 3). The organic layer was washed with aqueous saturated sodium bicarbonate, dried by sodium sulfate, ltered and concentrated in vacuum. Purication by ash column chromatography gave the desired product 2a (2a-2c).A mixture of iodobenzene (6.82 mmol), 1a (0.70 g, 6.20 mmol), 8-hydroxyquinoline (0.09 g, 0.62 mmol), cuprous iodide (0.18 g, 0.62 mmol) and potassium carbonate (1.73 g, 12.40 mmol) in DMSO (10 mL) was heated at 135 oC for 20 h. After cooling to room temperature, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate, dried by sodium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography gave the desired products 2d (2d-2g).

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-Nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

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,
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Adding a certain compound to certain chemical reactions, such as: 1572-10-7, name is 3-Amino-5-phenylpyrazole, 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 1572-10-7, HPLC of Formula: C9H9N3

General procedure: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.

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Reference:
Article; Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin; Chinese Chemical Letters; vol. 31; 2; (2020); p. 418 – 422;,
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Reference of 57999-06-1, These common heterocyclic compound, 57999-06-1, name is 4-Phenyl-1H-pyrazol-5-amine, 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: The suitable 4-substituted-5-aminopyrazoles (1c-f, 1h-p) (20 mmoles) were diazotized as usual and the solution of diazonium salt was treated with of sodium acetate (24 mmoles) at room temperature and stirred until to complete dissolution. At this solution was then added ethyl acetoacetate (20.0 mmoles) in ethanol and stirred for 1 h at room temperature. The final compounds were recovered by filtration after addition of water or by extraction if a precipitate was not formed. Starting from 1f, in this reaction condition, a byproduct is formed and identified as 1H-Benzo[h]pyrazolo[3,4-c]cinnoline, 10. The unambiguous synthesis of this latter was obtained as described below. 5.6.1 Ethyl 4-methyl-8-(pyridin-3-yl)pyrazolo[5,1-c][1,2,4]triazin-3-carboxylate, 7c ;Yellow crystals; TLC eluent: dichloromethane/methanol 10:1 v/v; 1H NMR (CDCl3) delta 9.41 (d, J?=?2.0?Hz, 1H, Py); 8.77 (s, 1H, H-2); 8.70 (dd, J?=?7.8, 1.7?Hz, 1H, Py); 8.22 (dd, J?=?4.9, 1.7 1H, Py); 7.49 (dd, J?=?7.8, 4.9, 1H, Py); 4.60 (q, J?=?7.0?Hz, 2H, CH2); 3.27 (s, 3H, CH3); 1.60 (t, J?=?7.0?Hz, 3H, CH3). ;Anal C, H, N.

The synthetic route of 57999-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guerrini, Gabriella; Ciciani, Giovanna; Daniele, Simona; Martini, Claudia; Costagli, Camilla; Guarino, Chiara; Selleri, Silvia; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2475 – 2487;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2075-45-8, The chemical industry reduces the impact on the environment during synthesis 2075-45-8, name is 4-Bromo-1H-pyrazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-bromo-1H-pyrazole (0.1 g, 0.68 mmol) in DMF (20 ml) were added K2CO3 (0.19 g, 1.36 mmol, 2 eq.) and (bromomethyl)cyclopropane (92 mg, 0.68 mmol, 1 eq.). The mixture was stirred at RT for 4 h. The mixture was quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude product (0.15 g).

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-Bromo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (2015); A1;,
Pyrazole – Wikipedia,
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Application of 118430-74-3, These common heterocyclic compound, 118430-74-3, name is 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine, 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: A 0.1 M NaClO4solution (50 ml) in MeCN containing NH4SCN (6 mmol, 0.46 g) and indole (1a)(2 mmol, 0.24 g) was placed in a glass cell with coaxally positioned Ptelectrodes (San. = 26 cm2, Scat. = 10 cm2). The electrolysis was performed atE = 0.70 V vs SCE (CPE) or at j = 2.5 mA/cm2 (GE). After passing of 2.1 F ofelectricity in CPE (or 2.5 F in GE) calculated on the basis of 1 F/NH4SCN mol, theelectrolysis was terminated and the MeCN was distilled off. H2O (10 ml) wasadded and the residue was extracted with CH2Cl2 (4 25 ml). The extractswere combined, dried over anhydrous Na2SO4, filtered and the solvent wasdistilled off. The residue was purified by column chromatography on silica gel(eluent-a mix of light petroleum and EtOAc with a buildup of the volumefraction of the latter from 5% to 20%) to afford pure 3-thiocyanato-1H-indole

Statistics shows that 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine is playing an increasingly important role. we look forward to future research findings about 118430-74-3.

Reference:
Article; Kokorekin, Vladimir A.; Sigacheva, Vera L.; Petrosyan, Vladimir A.; Tetrahedron Letters; vol. 55; 31; (2014); p. 4306 – 4309;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate, molecular formula is C6H9N3O2, 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. Quality Control of Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate

Synthesis of compound 3d: 4-(3-{3-[5-(tert-Butoxycarbonylamino-methyl)-pyridin-3-yl]-6-oxo-6H-pyridazin-1-ylmethyl}-benzoylamino)-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester A mixture of 3-{3-[5-(tert-Butoxycarbonylamino-methyl)-pyridin-3-yl]-6-oxo-6H-pyridazin-1-ylmethyl}-benzoic acid lithium salt (240.0 mg; 0.54 mmol; 1.0 eq.), (benzotriazol-1-yloxy)tris(dimethylamino)-phosphonium hexafluorophosphate (321.5 mg; 0.71 mmol; 1.3 eq.) and ethyldiisopropylamine (0.14 ml; 0.81 mmol; 1.5 eq.) in DMF (3 ml) was stirred at rt for 4 h. The reaction mixture was poured into water and extracted with ethyl acetate, washed with brine and concentrated to yield the crude title compound as off-white solid (310.0 mg; yield: 100%), which was used for next step without further purification. LC-MS (M+H)+: 574.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 637336-53-9, its application will become more common.

Reference:
Patent; Merck Patent GmbH; CHEN, Xiaoling; LAN, Ruoxi; JORAND-LEBRUN, Catherine; YU, Henry; GOUTOPOULOS, Andreas; (34 pag.)US2016/229871; (2016); 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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1H-Pyrazole-4-carbonitrile

To a solution of 2-chloro-N-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide (15.0 g, 38.8 mmol) in acetonitrile (450 mL) were added 1H-pyrazole-4-carbonitrile (5.41 g, 93.1 mmol) and powdered potassium carbonate (16.1 g, 116 mmol) and it was stirred overnight at 10000. The reaction mixture was concentrated in vacuo and the residue was extractedwith ethyl acetate and water. Pure title compound precipitated and was filtered off (9.09 g20.5 mmol, 53 % yield, 97 % purity), The organic phase was washed with brine and dried over sodium sulfate. Concentration in vacuo led to further crude title compound (9.11 g., app. 60 % purity).LC-MS (Method B): Rt = 1.17 mm; MS (ESIneg): m/z = 442 [M-H]1HNMR (400MHz, DMSO-d6) oe [ppm]: 3.53 (s, 3H), 3.64 (s, 3H), 4.08 (s, 2H), 6.20 (d,1H), 6.29 (dd, 1H), 7.07 (d, 1H), 7.89 (d, 1H), 8.12 (br s, 1H), 8.30 (br s, 1H), 8.41 -8.54 (m, 2H), 9.17 (brs, 1H).

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

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

Reference of 35344-95-7, 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 35344-95-7 as follows.

A solution of 1H-pyrazole-4-carbaldehyde (2.05 g, 21.4 mmoL) and hydroxylamine hydrochloride (1.63 g, 23.5 mmol) in MeOH (50 mL) was stirred at room temperature for 19 hrs. The reaction mixture was concentrated to give 1H-pyrazole-4-carbaldehyde oxime (3.3 g, crude) as a yellow solid.

According to the analysis of related databases, 35344-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics