Day: August 16, 2021

1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, 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. Formula: C4H7N3

General procedure: Amino-pyr azole 1 (0.291 g, 0.003 mol) and an aqueous solution of NaBr (100 mL) (concentrations were as follows: 1 in entries 1 and 2, 2 Min entries 3 and 5-9, and 3 in entry 4) were placed in a cell. In experiment 2, NaHCO3 (0.504 g, 0.006 mol) was added to the solution. The electrolysis was carried out at the following currents: 426 mA for entries 1-4, 213 mA for entry 5, 710 mA for entries 6, 8, and 9, and 852 mA for entry 7. In experiment 9, 48% aqueous solution of HBr was periodically added to the reaction mixture to maintain 7. After passing 2 F of electricity per 1 mole of the starting aminopyrazole 1(Q= 579 C) for entries 1-7or 8 F (Q= 2316 C) for entries 8and 9, the electrolysis was stopped, the reaction mixture was stirred for 1 h and analyzed by TLC (eluent light petroleum ether-ethyl acetate (1 : 1)). Then, the mixture obtained was diluted with concentrated HCl (to 3) and the products were extracted with CHCl3 (3×30 mL). The extracts were combined, dried with anhydrous MgSO4, and concentrated in vacuo. The products were isolated using column chromatography on SiO2 (eluent light petroleum ether-ethyl acetate). The following compounds were isolated: 1,2-bis(1-methyl-1H-pyrazol-3-yl)-diazene (7) (entries 1-7; the product was identified by m.p. 201-202 C (cf. Refs 2 and 4: m.p. 201 C) and the reported 2,41 NMR spectra) and 1,2-bis(4-bromo-1-methyl-1H-pyrazol-3-yl)diazene (8) (entries 8 and 9, the product was identified by NMR spectroscopy and high resolution mass spectrometry). The aqueous layer obtained after extraction was concentrated in vacuo, diluted with NaOH with stirring (to 10), and treated as described above. This resulted in the isolation of 3-amino-4-bromo-1-methyl-1H-pyrazole (6) (entries 1-9; the product was identifi ed by m.p. 97 C (cf. Ref. 10: m.p. 97-98 C) and the reported 51 NMR spectra) and unreacted aminopyr-azole 1(entries 1-8; the starting compound was identified by TLC and NMR spectroscopy).

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lyalin; Sigacheva; Kokorekin; Dutova, T. Ya.; Rodionov; Petrosyan; Russian Chemical Bulletin; vol. 67; 3; (2018); p. 510 – 516; Izv. Akad. Nauk, Ser. Khim.; 3; (2018); p. 510 – 516,7;,
Pyrazole – Wikipedia,
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Electric Literature of 42027-81-6,Some common heterocyclic compound, 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, molecular formula is C5H7N3O3, 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: 2a (0.32 g, 0.002 mol) was dissolved in 20 ml ethanol in a roundbottomedflask and Pd/C (10%, 0.1 g) was added which reacted at 60 Cfor 12 h under hydrogen atmosphere. The Pd/C was recycled by filtrationand the ethanol was recycled by evaporation to give the amineas purple oil which was retained in the round-bottomed flask. Theamine was used for next reaction without purification, because it waseasily oxidized. Then, added 6-bromo-4-chloroquinazoline (0.36 g,0.0015 mol) and isopropanol (30 ml) to the round-bottomed flask aboveand stirred at 90 C for 4 h. The isopropanol was removed under reducedpressure and the residue was purified through a column chromatographyon silica with chloroform/methanol (V:V 10:1) as a whitesolid (0.43 g, 86.0% yield).

The synthetic route of 42027-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Huai-Wei; Wang, Shu; Qin, Xiao-Chun; Wang, Jian; Song, Hong-Rui; Zhao, Qing-Chun; Song, Shao-Jiang; Bioorganic and Medicinal Chemistry; vol. 27; 13; (2019); p. 2729 – 2740;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application 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.

A mixture of 3-tert-butyl-1H-pyrazol-5-amine 7 (0.139 g, 1 mmol), methyl ester 6 (0.199 g, 1 mmol) and DMSO (2 mL) was stirred at ambient temperature during 2 h. After complete disappearance of the starting materials (monitored by TLC), the solid formed was collected by filtration and washed with MeOH/H2O (1/2) (3 × 2 mL), to afford compound 8. Orange solid, 76% yield; m.p: 241-242 C. FTIR nu (cm-1): 3371 (NH), 3316 (NH), 3117, 2955, 1705 (CO), 1625 (CN), 1532 and 1323 (NO2), 1122 (C-O); 1H NMR (CDCl3) delta 1.39 (s, 9H, tBu), 3.95 (s, 3H, OCH3), 5.98 (s, 1H, Pz-CH), 8.06 (d, 1H, J = 9.1 Hz), 8.13 (dd, 1H, J = 9.1 Hz, J = 1.8 Hz), 8.94 (d, 1H, J = 1.8 Hz), 10.07 (bs, 1H, Pz-NH) ppm, the aniline NH is missing; 13C NMR (CDCl3) delta 30.0 (tBu), 31.2 (Cq, tBu), 52.2 (OCH3), 94.9 (Pz-CH), 117.2, 119.5 (Cq), 128.9, 132.1 (Cq), 136.2, 144.3 (Cq), 148.0 (Cq), 154.6 (Cq), 165.5 (CO) ppm. MS (EI) m/z (%): 318 (100, M+), 287 (15, M – CH3). Anal. Calcd. for C15H18N4O4: C, 56.60; H, 5.70; N, 17.60. Found: C, 56.54; H, 5.83; N, 17.46.

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:
Article; Abonia, Rodrigo; Cortes, Edwar; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4062 – 4070;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 120068-79-3, A common heterocyclic compound, 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, molecular formula is C11H5Cl2F3N4, 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.

0.01 mol of 5-amino-1-(2,6-dichloro-4-trifluoromethyl)-3-cyano-1H-pyrazole was added to a four-necked flask.Heated to 90 C,3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane formyl isocyanate 0.01 mol and 5 ml of toluene solution were added dropwise.The reaction was refluxed for 5 h.After the reaction is completed, the crystals are cooled and filtered, and filtered.The filter cake was recrystallized from ethanol to give the product 4.82 g. The yield was 81.9%.

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 Tech University; Wan Rong; Qin Xiaofei; Shen Chen; Guo Chunwei; Wu Shaohua; Han Zhenyu; Chen Fuli; (9 pag.)CN104829538; (2018); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4522-35-4, A common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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.

INTERMEDIATE 30 4- (3-Iodo-lH-pyrazol-l-yl)-2-methoxy-5-(trifluoromethyl)pyridine To a solution of 3-iodopyrazole (0.30 g, 1.547 mmol), in DMSO (7.73 mL) was added sodium hydride (60% in oil, 0.068 g, 1.701 mmol) and stirred for 0.5 h before 4-iodo- 5- trifluoromethyl-2-methoxypyridine (0.469 g, 1.547 mmol) was added. The reaction mixture was stirred at 80 C for 4 h. The reaction was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 24 g, 0-20 % EtOAc in hexanes) to give 4-(3-iodo-lH-pyrazol-l-yl)-2-methoxy-5-(trifluoromethyl)pyridine, as a white solid. LCMS calc. = 369.96; found = 369.83 (M+H)+. NMR (500 MHz, CDC13): delta 8.58 (s, 1 H); 7.63 (s, 1 H); 7.01 (d, J ^ 2.8 Hz, 1 H); 6.65 (d, J= 2.6 Hz, 1 H); 4.03(d, J= 3.3 Hz, 3 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; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5203-77-0, 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. 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, This compound has unique chemical properties. The synthetic route is as follows.

At room temperature, 1,3-dimethyl-1hydro-pyrazole-5-ol (0.65 g, 0.0058 mol) and (0.48 g, 0.012 mol) sodium hydroxide were sequentially dissolved in 20 ml of dichloromethane.The low temperature bath was cooled to -4 C. To the above mixture was added dropwise 3,7-dichloro-5-(methylsulfonyl)-6-(((tetrahydrofuran-3-yl)methoxy)methyl)quinoline-8-carbonyl chloride (3.81 g, 0.0084 mol),The dropping rate was 4 drops / 30 seconds. After the addition was complete, the mixture naturally rose to room temperature and reacted for 5 hours.To the reaction mixture was added 10 ml of a saturated aqueous sodium hydrogen carbonate solution, and dichloromethane (3 * 15 ml) was extracted. The organic layers were combined, washed with water (1 * 15 ml), washed with saturated brine, and dried over anhydrous magnesium sulfate.The product was dissolved under reduced pressure to obtain 2.12 g of the product with a yield of 70%

The chemical industry reduces the impact on the environment during synthesis 1,3-Dimethyl-1H-pyrazol-5-ol. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong Joint Pesticide Co., Ltd.; Tang Jianfeng; Chi Huiwei; Wu Jianting; Yuan Xue; Liu Ying; (52 pag.)CN110615781; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35277-02-2, name is 4-Fluoro-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 35277-02-2, SDS of cas: 35277-02-2

To a solution of 4-fluoro-1H-pyrazole (0.09 g, 0.001048 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.15 g, 0.003669 mol). After addition, the resulting mixture was stirred for three hours. (R)-3-Bromo-N-(4-cyano-2-iodo-5-(trifluoromethyl)phenyl)-2-hydroxy-2- methylpropanamide (0.50 g, 0.001048 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at room temperature under argon. The reaction was quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under vacuum. The product was purified by a silica gel column using hexanes and ethyl acetate (2:1 to 1:1) as eluent to afford 0.32 g (64%) of the titled compound as a white solid.1H NMR (400 MHz, CDCl3) d 9.60 (s, 1H, NH), 8.76 (s, 1H, ArH), 8.69 (s, 1H, ArH), 7.76 (d, J = 4.8 Hz, 1H, Pyrazole-H), 7.36 (d, J = 4.4 Hz, 1H, Pyrazole-H), 6.85 (s, 1H, OH), 4.39 (d, J = 14.0 Hz, 1H, CH), 4.20 (d, J = 14.0 Hz, 1H, CH), 1.41 (s, 3H, CH3).Mass (ESI, Negative): 481.00 [M-H]-;

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; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane, D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (202 pag.)WO2019/222556; (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. 7119-95-1, name is 1-Nitropyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 7119-95-1

3-Nitro-lH-pyrazolew; [539] [Ref.: Janssen, J.W.A.M. and Habraken, C.L., J. Org. Chem., 1971,36,3081.] A solution of l-nitro-ll/’-pyrazole (3.0g, 0.026 mol) in anisole (200mL) was heated at 145C overnight. The mixture was cooled to rt, the white solid was collected by filtration and washed with hexanes. The mother liquid was diluted with hexanes (500mL) and cooled to -20C, and the resulting off-white solid was collected and combined with the previous solid.LC-MS (ES, Pos.): 1 14 [MH+]. ‘H NMR (DMSO-d6, 400 MHz): 5 = 7.04 (d, J= 2.5 Hz, 1H),8.04 (d, /= 2.5 Hz, 1H), 13.96 (br s, 1H).

The synthetic route of 7119-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
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 5775-82-6 as follows. name: 4-Bromo-1,3-dimethyl-1H-pyrazole

To a suspension of 4-bromo-l,3-dimethyl-pyrazole (5.00 g, 28.60 mmol) in anhydrous 1,4-dioxane (100.0 mL) were added 4,4,4′,4′,5,5,5′,5l-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (8.71 g, 34.32 mmol), acetoxy potassium (5.63 g, 57.41 mmol) and Pd(dppf)2Cl2 dichloromethane complex (2.38 g, 2.86 mmol). The mixture was degassed and refilled with nitrogen for several times and then heated to 100 C and stirred overnight. The mixture was concentrated in vacuo. The residue was diluted with water (30 mL), and the resulting mixture was extracted with EtOAc (50 mLchi3). The combined organic layers was dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica chromatography (EtOAc/PE (v/v) = 1/20 to 1/8) to afford the title compound as brown sticky liquid (3.80 g, yield 60%).MS (ESI, pos. ion) m/z: 223.3 [M+H]+

According to the analysis of related databases, 5775-82-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Xiaobo; LI, Mingxiong; ZHANG, Tao; HU, Haiyang; WU, Yanjun; (139 pag.)WO2018/169700; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

10199-68-5, name is 4-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. Quality Control of 4-Phenyl-1H-pyrazole

To a solution of l,2-dibromoethane (130 mg, 0.694 mmol) and 4-phenyl-lH- pyrazole (100 mg, 0.694 mmol) in DMF (2 mL) was added CS2CO3 (226 mg, 0.694 mmol) portion-wise. The mixture was stirred at RT for 30 min and at 65 C for 1.5 hrs. LCMS showed the starting material was consumed completely and product was detected. The mixture was poured into water (10 mL) and extracted with ethyl acetate (10 mL*3). The combined organic layers were washed with brine (10 mL), dried over NaiSOr. filtered and concentrated to residue. The residue was purified by prep-TLC (pet. etherethyl acetate; 2: 1) to give the desired product l-(2-bromoethyl)-4-phenyl-lH-pyrazole (60 mg, 0.239 mmol, (0989) 34.4 % yield) as yellow oil. LCMS (M +H) = 251.0; Retention time (10 mM NH4HC03) = 1.40 min.

The synthetic route of 10199-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; GILLIS, Eric P.; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M.; (367 pag.)WO2019/244066; (2019); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics