Day: September 6, 2021

Electric Literature of 1453-58-3, 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. 1453-58-3 name is 3-Methylpyrazole, 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.

Potassium /-butoxide (3.9 g, 0.33 mmol) was dissolved in DMSO (25 mL). To this solution was added 3 -methyl pyrazole (2.7 g, 0.33 mmol) and the reaction was heated at 50 °C for 30 min. l-Bromo-4-chloro-2-fluorobenzene (4.6 g, 0.22 mmol) was then added and the reaction was stirred at 50 °C for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, and dried over Na2S04) filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtO Ac/heptane) provided l-(2- bromo-5-chlorophenyl)-3-methyl-lH-pyrazole and l-(2-bromo-5-chloroplienyl)-5-methyl-lH- pyrazole as a 4: 1 mixture that was used in the next step directly,

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

Reference:
Patent; KAROS PHARMACEUTICALS, INC.; DE LOMBAERT, Stephane; GOLDBERG, Daniel R.; BRAMELD, Kenneth; SJOGREN, Eric Brian; SCRIBNER, Andrew; WO2015/35113; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 23170-45-8, These common heterocyclic compound, 23170-45-8, name is Methyl 3-methyl-1H-pyrazole-4-carboxylate, 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.

Synthesis of methyl l-benzyl-S-methyl-lH^yrazole-4-carboxylate. [00186] To a solution of methyl 3-methyl-lH-pyrazole-4-carboxylate (280 mg, 2 mmol) in N, N-dimethylformamide (30 mL) was added (bromomethyl)benzene (0.34 g, 2 mmol) and potassium carbonate (0.55 g, 4 mmol). The mixture was stirred at 20 C and stirred for 12 hours. The solvent was evaporated in vacuo and the residue was purified by CXTH (Column:Dsisol, 10muMu, CI 8, 250 mm*50 mm; Mobile: aeetonitrile(0.1% formic acidj-water (0.1% formic acid), acetonitrile from 30% to 70% in 80 minutes; oven; 20C; flow rate: 50 mL/minute, wavelength; 214 nm) to give crude methyl 1 -benzyl-5-meth.yl- lH-pyrazole-4-earboxylate (200 mg, 42%). LRMS (M + H+) m/z calcd. 230.1 1 ; found 230.

Statistics shows that Methyl 3-methyl-1H-pyrazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 23170-45-8.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew, S.; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NAVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2013/120104; (2013); 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. 56984-32-8, name is Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

The 1 – methyl -5 – chlorine pyrazole -4 – formic acid ethyl ester (300 mg, 1 . 59 mmol), phenol (300 mg, 3 . 19 mmol) dissolved in DMF, is added cesium carbonate (1.52, 4 . 66 mmol), microwave reactor 130 C reaction 30 minutes, the reaction is finished, to be reaction liquid cooling to room temperature, poured into water, extracted with ethyl acetate, the organic layer using saturated salt water washing, drying of the organic layer, dryness, passes through the rapid preparation column purification product 280 mg, yield is 72%.

The synthetic route of 56984-32-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shen Jianhua; Leng Ying; Zou Qingan; Ning Mengmeng; (116 pag.)CN105164112; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 20154-03-4, 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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

NaH (33.08 g (19.85 mol, 60 percent) was washed with n-hexane, then dry DMF (500 mL) was added drop wise under N2 atmosphere and the mixture was stirred well. A solution of 3- (trif luoromethyl)- 1 H-pyrazole (75 g, 0.55 mol) in DMF (125 mL) was added drop wise under N2 atmosphere. Then a solution of 4-methoxylbenzyl chloride (86.3 g, 0.55 mol) in DMF (125 mL) was added drop wise and the overall reaction mixture was allowed to stir for 12 h at room temperature. Progress of the reaction was monitored by TLC (10 percent ethyl acetate/hexane, Rf~0.4). On completion of the reaction, the reaction contents were poured into ice water (500 mL) and the product was extracted with ethyl acetate (2 Chi 400 mL). The ethyl acetate layer was washed with 2N HCI (2 x 200ml). Then the contents were dried over sodium sulfate and concentrated under reduced pressure. The obtained crude was purified by CC with 10percent ethyl acetate/n-hexane to yield 1 -(4-methoxybenzyl)-3-(trifluoromethyl)-1 H- pyrazole as a brown colored liquid (98 g, 70 percent). 400 mL). The ethyl acetate layer was washed with 2N HCI (2 x 200ml). Then the contents were dried over sodium sulfate and concentrated under reduced pressure. The obtained crude was purified by CC with 10percent ethyl acetate/n-hexane to yield 1 -(4-methoxybenzyl)-3-(trifluoromethyl)-1 H- pyrazole as a brown colored liquid (98 g, 70 percent).

The synthetic route of 3-(Trifluoromethyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68464; (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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

Synthesis of N-Boc-N’-n-octyl-1-guanylpyrazole Under ice-cooling and under nitrogen atmosphere, to a suspension of NaH (60% in oil, 283 mg, 7.08 mmol) in DMF (10 mL)) was added N,N’-bis-Boc-1-guanylpyrazole (2 g, 6.44 mmol) by small portions. After stirring at the same temperature for 15 min, 1-iodooctane (2.33 mL, 12.9 mmol) was added dropwise, and the mixture was stirred overnight while raising the temperature to room temperature. Under ice-cooling, water was added to discontinue the reaction, and the whole mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl solution, and dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography using n-hexane:AcOEt=8:1 as an eluate to give the object product as an oil (yield: 1.8 g, 66.1%). 1H NMR (300 MHz, CHLOROFORM-d) deltappm 0.78-0.92 (3H, m), 1.19-1.36 (10H, m), 1.27 (9H, s), 1.50 (9H, s), 1.65-1.81 (2H, m), 3.61-3.69 (2H, m), 6.41 (1H, dd, J=2.7, 1.6 Hz), 7.69 (1H, d, J=1.1 Hz), 7.93 (1H, br. s.)

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2012/172293; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 132712-71-1, 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. 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 5-Amino-4-arylazo-3-methyl-1-phenylpyrazoles (0.01 mol) weredissolved in a mixture of glacial acetic acid and concentrated hydrochloricacid (20 ml, ratio 1:1) and the solutionwas then cooled to 0-5 C. Sodiumnitrite (0.69 g, 0.01 mol) in water (10 ml) was then added to this solution dropwise with vigorous stirring, for about 1 h, while cooling at0-5 C. Then the resulting diazonium solution was added in portionsover 30 min to a vigorously stirred solution of 5-hydroxy-3-methyl-1H-pyrazole or 5-hydroxy-3-methyl-1-phenylpyrazole (0.01 mol) in KOH (0.56 g, 0.01mol) andwater (10ml) between 0 and 5 C,maintainingthe pHat 7-8 by simultaneous sodiumacetate solution addition. The mixture was then stirred for 2 h at 0-5 C. The precipitated product separated upon dilution with water (50 ml) was filtered off, washed with water several times, dried and crystallized from DMF-H2O

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

Reference:
Article; Karci, Fikret; Bakan, Emine; Journal of Molecular Liquids; vol. 206; (2015); p. 309 – 315;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 133228-21-4, 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. 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of N,N-dimethyl-1H-pyrazole-1-sulfonamide obtained in Step A (6.74 g) in tetrahydrofuran (75 mL) was added dropwise n-butyllithium hexane solution (1.3 M, 31.1 mL) over 15 min at -78C. The reaction mixture was stirred at -78C for 15 min, and a solution of 1,2-dibromo-1,1,2,2-tetrachloroethane (13.8 g) in tetrahydrofuran (25 mL) was added dropwise thereto over 10 min. The reaction mixture was stirred at -78C for 15 min, and then at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.03 g). 1H NMR (400 MHz, CDCl3) delta 3.06 (6H, s), 6.42 (1H, d, J = 1.6 Hz), 7.60 (1H, d, J = 1.6 Hz)

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, N,N-Dimethyl-1H-pyrazole-1-sulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3273-44-7, name is 5-Methyl-1H-pyrazole-3-carbaldehyde, molecular formula is C5H6N2O, 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. SDS of cas: 3273-44-7

EXAMPLE 15 7,7-Dimethyl-2-(5-methylpyrazol-3-yl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one Analogously to Example 2, starting from 0.57 g. (3 mmol) 5,6-diamino-3,3-dimethylindolin-2-one and 0.33 g. (3 mmol) 5-methylpyrazole-3-aldehyde, there is obtained the crude product after rendering the reaction mixture alkaline with concentrated aqueous ammonia solution. The residue is purified over silica gel (elution agent: methylene chloride/ammonia-saturated methanol 10:3 v/v). Yield: 0.22 g. (26% of theory); m.p. 245-250 C., crystallized from water.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3273-44-7, its application will become more common.

Reference:
Patent; Boehringer Mannheim GmbH; US4835280; (1989); A;; ; Patent; Boehringer Mannheim GmbH; US4695567; (1987); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 152120-54-2,Some common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, molecular formula is C14H22N4O4, 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.

To a stirred solution of N,N?-di-Boc-pyrazologuanidine (1,0 g, 3,22 mmol) in dry THF (20 mL) under N2 atmosphere, PPh3 (1,27 g, 4,19 mmol) and crotyl alcohol (0,36 mL, 4,19 mmol) were added. The mixture was cooled to 0 Cand DIAD (0,91 mL, 4,84 mmol) was added dropwise. The mixture was stirred at 0 C for 15 min then at room temperature for 2 h, then it was diluted with AcOEt and washed with water. The aqueous phase was back-extracted with AcOEt. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified with flash chromatography on silica gel, eluting with 10% AcOEt/Hex to give pure compound 9 (0.95 g, 95% yield). 1H NMR (400 MHz CDCl3) delta 7.89 (s, 1H), 7.66 (s, 1H), 6.37 (s, 1H), 5.60 (m, 2H), 4.18 (m, 2H), 1.62 (s, 3H), 1.44 (s, 9H), 1.22 (s, 9H). LC-MS(ES) m/z = 387.1 [M+Na]+, 365.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, its application will become more common.

Reference:
Article; Borgini, Matteo; Orofino, Francesco; Truglio, Giuseppina I.; Balestri, Lorenzo; Botta, Maurizio; Arkivoc; vol. 2019; 4; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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 1-Methyl-1H-pyrazole-4-carbaldehyde

1-methyl-1H-pyrazole-4-carbaldehyde previously obtained, malonic acid (4.68g, 45mmol), pyridine (4ml, 50mmol) and piperidine (0.09ml, 1mmol) were placed in a 250 ml flask and heated at 110C for 6h under nitrogen, then the reaction was stopped and cooled. The resulting solution was added with water (100ml), followed by addition of strong aqua dropwise to dissolve all the solids. The solution was then brought to pH~1 with concentrated hydrochloric acid. The precipitate thus obtained was collected by filtration, washed with water several times and then dried in vacuo to give the title compound (2.9g). 1H-NMR (d6-DMSO, 300 MHz) delta3.83 (s, 3H), 6.17 (d, 1H, J=16.2), 7.45 (d, 1H, J=15.9), 7.83 (s, 1H), 8.07 (s, 1H), 12.07 (s, 1H).

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; WANG, Kai; EP2725024; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics