Day: July 8, 2021

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. 1780-72-9, name is 4-Bromo-5-methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Computed Properties of C4H6BrN3

General procedure: Kinetics of reactions were followed using stopped-flow technique by measuring the change in absorbance as a function of time at suitable wavelengths. The working wavelengths were determined by comparing consecutive spectra of the reaction mixture over the wavelength range 200-600 nm. The reactions were studied under the pseudo-first-order conditions, which means that the concentration of entering ligand was always much higher (at least a 10-fold times) than the concentration of complex ([complex]e = 1 * 10-4 M, [ligand]e = from1 * 10-3 M to 5 * 10-3 M). Reactions were initiated in the stopped-flow instrument by mixing equal volumes of complex solution and entering ligand solution. Reactions were followed for at least eight half-lives. Kinetic traces were fitted as a double-exponential function. The pseudo-first-order rate constants, kobsd1 and kobsd2,were obtained as average values from four to eight independent kinetic runs. All reactions were studied at three different temperatures (from 15 to 35 C) to determine the activation parameters.

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:
Article; Kosovi?, Milica; Ja?imovi?, ?eljko; Bugar?i?, ?ivadin D.; Petrovi?, Biljana V.; Transition Metal Chemistry; vol. 41; 2; (2016); p. 161 – 168;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1280210-79-8, The chemical industry reduces the impact on the environment during synthesis 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, I believe this compound will play a more active role in future production and life.

Intermediate 2(3.5g, 16.7mmol) dissolved in tetrahydrofuran (35 ml) in, 0 C adding of sodium hydride (1.0g, 25.4mmol, 60%), 30 minutes reaction, adding methyl sulfonyl chloride (2.9g, 25.4mmol) reaction 1 hour. Adding water to the reaction solution (10 ml) in the quenching of the reaction, ethyl acetate (50mL × 2) extraction, the combined organic layer, anhydrous sodium sulfate drying, concentration, silica gel column chromatography for purification (petroleum ether/ethyl acetate (v/v)=1:1), to obtain white solid3a(2.1g, yield 44%).

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, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LI, CAI-HU; WEI, YONG-GANG; (99 pag.)TW2017/8222; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 398491-59-3,Some common heterocyclic compound, 398491-59-3, name is tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate, molecular formula is C10H16N4O2, 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 solution of ethyl chlorocarbonate (8.9 ml, 93 mmol) in THF (250 ml) was added slowly to a mixture of 3-amino-4, 6-dihydro-lH-pyrrolo [3, 4-C] ole-5-carboxylic acid tert-butyl ester (20 g, 89 mmol) and DIISOPROPYLETHYLAMINE (DIEA, 92 ml, 528 mmol) in THF (500 ml) at 0-5C. The reaction was kept at the same temperature for two hours then allowed to reach room temperature and stirred overnight. The obtained mixture was evaporated to dryness under vacuum. The resulting residue was extracted with ethyl acetate and water. The organic phase was separated, dried over sodium sulfate and evaporated to dryness. The mixture was purified by flash-chromatography (eluent : ethyl ACETATE/EYCLOHEXANE 4/6 to 7/3) to give 19 g (72% yield) of the title compound as a white solid. 1H-NMR (400 MHZ, DMSO-S6) ppm: 10. 06 (S, broad signal, 2H), 4. 4-4. 05 (M, 6H), 1.27 (t, 3H) 1 (2, 9H).

The synthetic route of 398491-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA ITALIA S.P.A.; WO2004/80457; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 309740-49-6, A common heterocyclic compound, 309740-49-6, name is Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate, molecular formula is C6H7N3O4, 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.

B) Methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate To a solution of methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate (8.62 g) in methanol (100 mL), palladium-carbon (10%) (0.86 g) was added, and the mixture was stirred at room temperature for 4 hours in a hydrogen atmosphere (40 psi). Palladium-carbon was filtered off, and then, the filtrate was concentrated to obtain the title compound (4.71 g). 1H NMR (400 MHz, CDCl3) delta 3.91 (3H, s), 4.03 (3H, s), 4.15 (2H, brs), 7.07 (1H, s).

The synthetic route of 309740-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; ASANO, Yasutomi; KOJIMA, Takuto; KURASAWA, Osamu; WONG, Tzu-Tshin; HIRATA, Yasuhiro; IWAMURA, Naoki; SAITO, Bunnai; TANAKA, Yuta; ARAI Ryosuke; IMAMURA, Shinichi; YONEMORI, Kazuko; MIYAMOTO, Yasufumi; KITAMURA, Shuji; SANO, Osamu; (222 pag.)EP3287441; (2018); 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. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Quality Control of 1-Methyl-4-nitro-1H-pyrazole

Example 1 5-chloro-1-methyl-4-nitro-1H-pyrazole [0177] 4-nitro-1-H-pyrazole (5 g, 44.2 mmol) was added sodium hydroxide (1M, 200 mL) and dimethyl sulfate (31 mL, 330 mmol). The mixture was stirred at room temperature for 72 h and the mixture was extracted with CH2Cl2 (2×150 mL). The organic layer was separated and the solvent was distilled off to yield 1-methyl-4-nitro-1H-pyrazole as a white solid (4.30 g, 76%). [0179] Following WO 2007/99326, to a 500 mL 3-neck-round bottom flask was added 1-methyl-4-nitro-1H-pyrazole (4.30 g, 33.8 mmol) and THF (12 mL). The mixture was cooled to -78 C. and lithium hexamethyldisilazide in THF (1M, 88.4 mL, 90 mmol) was added dropwise via an addition funnel over 20 min. The brown mixture was stirred for 30 min and warmed to -45 C. over 30 min. The mixture was cooled back down to -78 C. and hexachloroethane (10.5 g, 44.2 mmol) dissolved in THF (20 mL) was added via an addition funnel over 15 min. The mixture was stirred for 2.5 h, warmed from -78 C. to -40 C. and the reaction was monitored by LCMS. Upon completion of the reaction, the reaction was quenched with a solution of saturated NH4Cl (150 mL), and ethyl acetate (100 mL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (150 mL), dried over Na2SO4 and the organic solvent was distilled off. The crude product was purified via flash chromatography (CH2Cl2/7% MeOH) to yield 5-chloro-1-methyl-4-nitro-1H-pyrazole as a white solid (1.40 g, 20%). 1H NMR (400 MHz, CDCl3) delta 8.13 (s, 1H), 3.92 (s, 3H); ESIMS m/z=162.0 (M+1)

The synthetic route of 3994-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3469-69-0,Some common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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.

Step 1 In a flask were combined 4-iodo-1H-pyrazole (1.00 g, 5.16 mmol), cyclopropylboronic acid (886 mg, 10.3 mmol) and sodium carbonate (1.09 g, 10.3 mmol) and the mixture suspended in 1,2-dichloroethane (20 mL). A suspension of copper (II) acetate (936 mg, 5.16 mmol) and 2,2-bipyridine (805 mg, 5.16 mmol) in 1,2-dichloroethane (40 mL) was warmed to 50 C. and added and the resulting mixture heated at 70 C. overnight. The mixture was then cooled and filtered and the solids rinsed with EtOAc. The combined filtrates were concentrated and the residue taken up in EtOAc and 50% saturated aqueous NH4Cl. The organic layer was washed with sat NH4Cl, sat NaHCO3 and sat NaCl and dried over MgSO4. The solution was concentrated and the residue purified by SiO2 chromatography (5-35% EtOAc/heptane) to afford 517 mg (43%) 1-cyclopropyl-4-iodo-1H-pyrazole as a colorless oil.

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2458-26-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2458-26-6 name is 3-Phenyl-1H-pyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To 3-phenyl-1H-pyrazole (188mg, 1.3mmol) in DMF (8mL) was added NaH (60% in oil, 60mg, 1.5mmol) and the solution was stirred for 5min. To the solution was added compound 78a (200mg, 1.Ommol) and the solution was heated to 6O0C for 1h. Allowed to cool, concentrated under vacuum, and purified by preparative TLC (30%EtOAc/hexanes) to yield compound 78b(61 mg, 20%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Phenyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2009/111442; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82231-58-1, These common heterocyclic compound, 82231-58-1, name is Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate, 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.

Step 3: Ethyl [4-(2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidin-5-yl)-1H-pyrazol-1-yl]acetateInto a 50-mL round-bottom flask equipped with a magnetic stirbar and reflux condenser was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidine (311 mg, 1.35 mmol), ethyl (4-bromo-1H-pyrazol-1-yl)acetate (400 mg, 0.89 mmol), PdCl2(dppf) (36 mg, 0.05 mmol), 2 M aqueous sodium carbonate solution (0.89 mL, 1.8 mmol) and DMF (4 mL). The resulting suspension was degassed under nitrogen for 20 min and then heated in the microwave to 120 C. for 20 min. The mixture was poured into a 125-mL separatory funnel containing a saturated aqueous KH2PO4 solution (50 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification by column chromatography through silica gel, eluting with 30% EtOAc in hexanes to 70% EtOAc in hexanes as a gradient gave the title compound as a white solid. MS (ESI, Q+) m/z 476 (M+1).

Statistics shows that Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate is playing an increasingly important role. we look forward to future research findings about 82231-58-1.

Reference:
Patent; Leblanc, Yves; Powell, David; Ramtohul, Yeeman K.; Leger, Serge; US2008/182838; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 4-fluorobenzonitrile (2.49 g, 20.6 mmol) and 4-formylpyrazole (1.98 g, 20.6 mmo) in 50 mL of DMF at 0 0C was added 95percent sodium hydride (0.54 g, 22.7 mmol) under nitrogen. The mixture was heated to 60 0C for 6 hours and cooled to room temperature, Water was added carefully and the mixture was then extracted with ethyl acetate. The combined extracts were washed with water and brine, and then dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude 4~(4-formyMH-pyrazol-l-yl)benzonitrile.

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, 1H-Pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; DI MARCO, Christina, Ng; WO2010/19391; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 187998-35-2, name is 1-(4-Chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid, 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. Computed Properties of C11H9ClN2O2

(3) Reference Example 1 [(trifluoromethyl) pyridin-5-yl] (3) 5-methyl-1 in -1H- pyrazole-4-carboxylic acid in place of Reference Example 6 in 1 – (4-chlorophenyl) -5-methyl -1H- pyrazole-4-carboxylic acid, the reaction process using the same acid under ice-cooling and the reaction mixture (281mg) by 1- (5-amino-3-cyano It was added to a pyridine solution of the no-2-yl) -4-cyano nopi piperidine (228mg) and, after stirring 0.25 hours at the same temperature, tri ethyl amine was added, was stirred at room temperature for 2 hours. After the reaction, water was added, and the precipitated solid was collected and then filtered, washed by suspension to give the title compound (425mg) as a white solid

The synthetic route of 1-(4-Chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics