Day: May 31, 2021

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 81945-73-5 as follows. Formula: C3H4N2O

EXAMPLE 7 6-Imidazolyl-2-(3,5-dimethoxy-s-triazin-1-yloxy)-1-[(1-pyrazolyl)-oxycarbonyl]-benzene 1.75 g (10.8 mmol) of N,N’-carbonylbisimidazole is added to a solution of 1.88 g (10 mmol) of 6-imidazolylsalicylic acid in 30 ml of tetrahydrofuran. After the mixture has been stirred for 30 minutes at room temperature, 9.9 mmol of N-hydroxypyrazole is added and the mixture is stirred for a further 14 hours. The reaction mixture is then hydrolyzed with 300 ml of 1N phosphoric acid and the resulting mixture is extracted several times with methyl tert-butyl ether. The organic phases are dried over sodium sulfate and evaporated down under reduced pressure. The residue is taken up in 40 ml of dimethylformamide, and 280 mg of sodium hydride (85% strength in paraffin, 10 mmol) is added. After the mixture has been stirred for 30 minutes at room temperature, 1.58 g (9 mmol) of 1-chloro-3,5-dimethoxy-s-triazine is added and the whole is stirred for 14 hours. The batch is introduced into 300 ml of 0.1N phosphoric acid, and extracted with diethyl ether. The ether phase is dried over sodium sulfate and evaporated down, and the residue is purified by column chromatography.

According to the analysis of related databases, 81945-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US5246914; (1993); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 10250-64-3, A common heterocyclic compound, 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, molecular formula is C11H10N2O2, 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: To a solution of 19 (1.2 eq) and HOBt(1.4 eq) in DMF (0.5 M) were added EDCI (1.3 eq) and a solution of 15a-j or 16a-j (1.0 eq) in DMF (0.25 M), Et3N (3.5 eq) at 0 C. The reaction mixture was stirred at room temperature for 24 hours, then diluted in AcOEt. The organic phase was washed with water twice, saturated aqueous NaHCO3 three times, and brine, then dried over Na2SO4,filtered, and concentrated. The residue was purified by flash column chromatography to give intermediates 17a-j and 18a-j.

The synthetic route of 10250-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 25; 23; (2015); p. 5619 – 5624;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1226781-82-3, 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 1226781-82-3 as follows.

Step (4) The distilled pale yellow wet product IV was dissolved in isopropyl acetate 35kg, and then added dropwise with acid solution at roomtemperature (benzenesulfonic acid 7.7kg and 14kg isopropyl acetate), stirring2d, suction filtration to give a pale gray solid, at 40 deg. C vacuum dried togive a pale gray solid after 10h 7.78kg, 95% yield, purity 98.2%.

According to the analysis of related databases, 1226781-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhongshan Yian Tai Pharmaceutical Co., Ltd.; Xu, Liang; Mao, Bo; Huang, Zhihong; Li, Yanxiong; (8 pag.)CN105348286; (2016); A;,
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. 95162-14-4, name is 4-Bromo-1-tritylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromo-1-tritylpyrazole

To a 500 mL Schenk flask backfilled with N2was added 4-bromo-1-trityl-1H-pyrazole(10.0 g, 25.7 mmol) and dry THF (250 mL). The resulting suspension was cooledto -78 C under stirring. 1.6 M n-butyl lithium (20.0 mL, 32.0 mmol, 1.2equiv.) was then added dropwise, and the solution was left to stir for 30minutes before adding triisopropyl borate (7.4 mL, 32.0 mmol, 1.2 equiv.)dropwise. The resulting solution was stirred at 1 hour at -78 C and allowed toreach room temperature over 1 hour. Pinacol (3.9 g, 33.4 mmol, 1.3 equiv.) wasadded under stirring, and the solution was stirred for 30 minutes before addingglacial acetic acid (1.6 mL, 28.3 mmol, 1.1 equiv.). The suspension was stirredfor a further 30 minutes before removing the solvent in vacuo to yield awhite solid. Recrystallization was achieved by triturating the crude compoundin DCM (3 mL) and methanol (200 mL) over 1 hour. The resulting solid wascollected by filtration, washed with methanol and dried overnight at 50 C toyield 1-trityl-1H-pyrazol-4-ylboronatepinacol ester (9.1 g, 20.9 mmol, 81.4%) as a white solid. 1H NMR (500 MHz, CD2Cl2) delta = 1.28(s, 12H), 7.12 – 7.14 (m, 6H), 7.30 – 7.33 (m, 9H), 7.63 (d, J = 0.9 Hz, 1H),7.81 (d, J = 0.9 Hz,). 13CNMR (125 MHz, CD2Cl2) delta = 25.17, 79.22, 83.82, 128.25,130.72, 139.35, 143.82, 145.83. HRMS(ESI) Calcd for C28H29BN2O2 [M+H]: 437.239983;Found: 437.240521.

According to the analysis of related databases, 95162-14-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kershaw Cook, Laurence J.; Kearsey, Rachel; Lamb, Jessica V.; Pace, Edward J.; Gould, Jamie A.; Tetrahedron Letters; vol. 57; 8; (2016); p. 895 – 898;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, 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 345637-71-0, Recommanded Product: 345637-71-0

A solution of 400 mg (0.77 mmol) of 1,1-dimethylethyl 4-[4-[[methyl[(l/?)-l- phenylethyl]amino]carbonyl]-2-thiazolyl]-l-piperidinecarboxylate (i.e. the product of Example 5, Step A) in 10 mL of a 1:1 mixture of methanol and dichloromethane was treated with 10 mL of 2 N hydrochloric acid in ether and stirred at room temperature for 4 h. The reaction mixture was concentrated on rotary evaporator, and the residue was three times treated with 10 mL of methanol followed by concentration to leave the crude piperidine hydrochloride. The reaction mixture was then dissolved in 10 mL of acetonitrile, and 1.O mL of triethylamine was added. Meanwhile, a solution of 310 mg (1.49 mmol) of 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetic acid in 10 mL of acetonitrile was treated with 1.0 mL of a solution of 1-propanephosphonic acid cyclic anhydride (50 % in ethyl acetate), stirred at room temperature for 15 minutes, then combined with the above amine solution. The reaction mixture was stirred at room temperature overnight, diluted with 50 mL of ethyl acetate, washed with 1 N aqueous hydrochloric acid, 1 N aqueous sodium hydroxide and brine, dried with MgSC^, filtered and concentrated under reduced pressure. Purification by Medium Pressure Liquid Chromatography (MPLC) on silica gel using ethyl acetate/methanol as eluant provided 330 mg of the title product, a compound of the present invention, as a white solid. 1H NMR (CDCl3) delta 1.60-1.80 (m, 5 H), 2.18 (m, 2 H), 2.30 (s, 3H), 2.80 (m, 5 H), 3.27 (m, 2 H), 4.00 (m, IH), 4.95 (s, 2 H), 5.79 and 6.14 (m, total IH), 6.35 (s, IH), 7.37 (m, 5H), 7.84 (s, IH).

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; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/91594; (2008); A2;,
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. 81945-73-5, name is 1H-Pyrazol-1-ol, A new synthetic method of this compound is introduced below., SDS of cas: 81945-73-5

(General Procedure 16)4-Methyl-piperazine-1-carboxylic Acid pyrazol-1-yl Ester The title compound was prepared from 1-hydroxypyrazole and N-methylpiperazine applying the general procedure 16. The crude product was purified by preparative HPLC (water-acetonitrile-0.1% TFA) (17%, salt with TFA). 1H NMR (300 MHz; CDCl3): delta 2.36 (s, 3H), 2.50 (bt, 4H), 3.59 (bs, 2H), 3.71 (bs, 2H), 6.31 (t, 1H), 7.38 (dd, 1H), 7.40 (dd, 1H); HPLC-MS: m/z=211.0 (M+1); Rt=0.40 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; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); 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. 151521-49-2, name is 4-Isopropyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Sodium (1.58 g, 68.7 mmol) was dissolved in EtOH (250 mL) and to this solution was added 4-isopropyl-lH-pyrazol-5-amine (3) (7.17 g, 57 mmol) and diethyl malonate (10.2 mL, 63 mmol). The solution was heated under reflux for 16 h, cooled to rt and concentrated in vacuo. The residue was dissolved in water (60 mL) and acidified to peta = 3 with 2 M HCl and the formed precipitate collected by filtration. The title compound ICEC0004 was obtained as an off-white solid (8.10 g, 35% over three steps). M.p. 242-2430C (ethanol).

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; EMORY UNIVERSITY; IMPERIAL COLLEGE OF SCIENCE AND TECHNOLOGY; JOGALEKAR, Ashutosh, S.; WO2008/151304; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, 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: 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid

To a 0C solution of 1 ,5-dimethyl- lH-pyrazole-4-carboxylic acid (1.0 g, 7.14 mmol) in DCM/MeOH (7 mL each) was added 2M TMSCHN2 in hexane (4.28 mL, 8.56 mmol). The reaction mixture was stirred at 0C for 1 h, then was allowed to warm to RT and stirred at RT overnight, then was concentrated in vacuo. The crude product was chromatographed (80 g Si02; continuous gradient from 0% to 50% EtOAc in hexane over 20 min) to give the title compound (900 mg, 5.84 mmol, 82 % yield). LCMS, [M + H]+ = 155.2.

The synthetic route of 31728-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; WANG, Ying; (140 pag.)WO2019/126085; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35691-93-1, 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. 35691-93-1, name is Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 8 1-Acetyl-azetidine-3-carboxylic Acid [(S)-3-[5-(3,5-dimethyl-1-pyrazin-2-yl-1H-pyrazole-4-carbonyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-1-(3-fluoro-phenyl)-propyl]-amide (III-25) 3,5-Dimethyl-1-pyrazin-2-yl-1H-pyrazole-4-carboxylic acid-To a solution of 3,5-dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester (1 g, 5.95 mmol) in DMF (20 mL) cooled to 0 C. was added portionwise NaH (60% in mineral oil, 171 mg, 7.13 mmol). After hydrogen evolution ceased, 2-chloro-pyrazine (0.64 mL, 7.13 mmol) was added and the reaction was stirred at 50 C. for 24 h. The reaction mixture was cooled to RT, partitioned between EtOAc and saturated NH4Cl. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified via SiO2 chromatography eluding with hexane/EtOAc to afford 0.64 g (44%) of 3,5-dimethyl-1-pyrazin-2-yl-1H -pyrazole-4-carboxylic acid ethyl ester.

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Lemoine, Remy; Melville, Chris Richard; Rotstein, David Mark; Wanner, Jutta; US2007/191335; (2007); A1;,
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 63680-90-0 as follows. Formula: C3H5Cl2N3

A 4-neck, 500-mL round bottom flask was charged with 3-chloro-1H-pyrazol-4-amine.HCl (15 g, 128 mmol), THF (50 mL), and water (50 mL). Sodium bicarbonate (32.2 g, 383 mmol) was added in portions to control off-gassing, and the mixture was cooled to 5 C. Acryloyl chloride (12.44 mL, 153 mmol) was added at <20 C. and the reaction was stirred for 2 h, after which the reaction was diluted with water (100 mL) and EtOAc (100 mL). The organic layer was concentrated to dryness to afford a white solid, which was suspended in MTBE (50 mL) and stirred for 2 h. The suspension was filtered and the solid was rinsed with MTBE (50 mL) to afford the desired product, N-(3-chloro-1H-pyrazol-4-yl)acrylamide (IIa), as a white solid after drying (14.8 g, 68% yield), mp: 182 C. (decomposition). 1H NMR (400 MHz, DMSO-d6) delta 12.96 (s, 1H), 9.77 (s, 1H), 8.10 (s. 1H), 6.58 (dd, J=17.0, 10.2 Hz, 1H), 6.23 (dd, J=17.0, 2.1 Hz, 1H), 5.73 (dd, 10.2, 2.1 Hz, 1H). 13C NMR (101 MHz, DMSO-d6) delta 162.69, 130.76, 130.14, 126.62, 123.60, 116.53. ESIMS: m/z 172.0 ([M+H]+). According to the analysis of related databases, 63680-90-0, the application of this compound in the production field has become more and more popular. Reference:
Patent; Dow AgroSciences LLC; Yang, Qiang; Lorsbach, Beth; Zhang, Yu; Walsh, Martin J.; Kister, Jeremy; (9 pag.)US2018/186752; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics