Tag: M.W:100-200

Electric Literature of 1260243-04-6, The chemical industry reduces the impact on the environment during synthesis 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Intermediate 18: Ethyl 7-(tert-butyl)-5-(4-ethylphenyl)-4,7-dihydropyrazolo[1,5- a]pyrimidine-3-carboxylateTo a solution of Intermediate 17 (1 g, 4.620 mmol) and ethyl 5-amino-1 H-pyrazole-4- carboxylate (ALDRICH, 0.717 g, 4.620 mmol) in 2-(methyloxy)ethanol (10 mL) was added TFA (0.885 mL, 1 1 .560 mmol) with ice-water cooling. The reaction was refluxed overnight. LCMS showed reaction was finished. The mixture was diluted with EtOAc, washed with saturated NaHC03, water and brine, dried over MgS04 and concentrated in vacuo. Then, the crude material was purified by flash chromatography on silica gel (Merck cartridge, 20 g) and was eluted with mixtures of hexane/EtOAc (80:20). The desired fraction was collected and evaporated to obtain a yellow solid (1.1 g, 3.1 10 mmol, 67%). 1H NMR (400 MHz, CDCI3) delta ppm: 7.73 (s, 1 H), 7.44 (d, 2H), 7.25 (d, 2H), 5.09 (dd, 1 H), 4.78 (d, 1 H), 4.30 (q, 2H), 2.68 (q, 2H), 1.37 (t, 3H), 1.26 (t, 3H), 0.92 (s, 9H). [ES+ MS] m/z 353 (M+H)+.

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, Ethyl 5-amino-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ALVAREZ-RUIZ, Emilio; BALLELL-PAGES, Lluis; CASTRO-PICHEL, Julia; ENCINAS, Lourdes; ESQUIVIAS, Jorge; GAMO-BENITO, Francisco Javier; GARCIA-PALANCAR, Maria Cruz; REMUINAN-BLANCO, Modesto Jesus; WO2012/143522; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-17-5, name is Methyl 5-methyl-1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O2, 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. Recommanded Product: 25016-17-5

General procedure: A mixture of 1 (5.68 mmol) and potassium tert-butoxide (7.59 mmol) in 80 ml of anhydrous THF was heated under reflux for 1 h. After cooling to 0 C, a solution of ethylbromoacetate (7.78 mmol) in 20 ml of THF was slowly added. The reaction mixture was then stirred for 5 h at room temperature. The resulting mixture was filtered and the solvent was evaporated to dryness. The obtained residue was purified on alumina using dichloromethane as eluant.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-17-5, its application will become more common.

Reference:
Article; Radi, Smaail; Yahyi, Abderrahmane; Ettouhami, Abdelkader; Chaudhary Jha, Ambika; Adarsh; Robeyns, Koen; Garcia, Yann; Polyhedron; vol. 85; (2015); p. 383 – 388;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-40-7,Some common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, molecular formula is C4H3N3O4, 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 solution of 4-nitro-1H-pyrazole-3-carboxylic acid (50.0 g, 318 mmol, CAS5334-40-7) in MeOH (250 mL) was added SOCl2 (56.8 g, 477 mmol). The mixture was stirred at 70 C. for 5 hrs. On completion, the mixture was concentrated in vacuo to give the title compound (54.0 g, 99% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) delta 14.40 (s, 1H), 9.98 (s, 1H), 3.89 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Nitro-1H-pyrazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1780-72-9, name is 4-Bromo-5-methyl-1H-pyrazol-3-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. Recommanded Product: 4-Bromo-5-methyl-1H-pyrazol-3-amine

To a solution of 2H-pyrazol-3-ylamine (2.3 mmol, 1 eq) in acetic acid (3 mL) was added 2-ethoxymethylene-malonic acid diethyl ester (500 muL, 2.5 mmol, 1.1 eq). The mixture was heated at 120 C. for 20 h in a sealed tube. After cooling, the precipitate was filtered and washed with ethanol to afford the expected compound (from 30% to 80% yield). [0595] The expected compound was obtained according to general procedure C step 1 using 4-bromo-5-methyl-2H-pyrazol-3-ylamine. The expected compound was isolated as pale yellow powder. [0596] MS: 300.0 [0597] Mp: decomposes at 270 C.-275 C.

The synthetic route of 4-Bromo-5-methyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; European Molecular Biology Laboratory; F. Hoffmann-La Roche AG; WOLKERSTORFER, Andrea; SZOLAR, Oliver; HANDLER, Norbert; CUSACK, Stephen; SAUVAITRE, Thibault; SIMON, Celine; MORICE, Christophe; GIETHLEN, Bruno; LANGER, Thierry; SMITH, Mark; SO, Sung-Sau; CLASSEN-HOUBEN, Dirk; BUSCHMANN, Helmut; US2013/317022; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

16461-94-2, name is 4-Bromo-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: C3H4BrN3

A. A solution of 3-amino-4-bromopyrazole (2.0 g, 12 mmol) and 1 ,1 ,3,3- tetramethoxypropane (4.1 mL, 25 mmol) in acetic acid (5 mL) was heated at reflux for 4 h. Water (2 mL) was added and the mixture heated at reflux for a further 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was triturated in methanol. The solid thus obtained was washed with cold methanol, ethyl acetate, and hexanes to provide 3-bromopyrazolo[1 ,5-a]pyrimidine as a brownish solid in 39% yield (0.953 g): 1H NMR (300 MHz, DMSO-d6) £9.13 (d, J = 6.5 Hz, 1 H), 8.61 (s, 1 H), 8.35 (s, 1 H), 7.19-7.02 (m, 1 H); MS (ES+) m/z 197.9 (M + 1), 199.9 (M + 1).

The synthetic route of 16461-94-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-3-methylpyrazole

4-Bromo-1-isopropyl-3-methyl-1H-pyrazole (B2.1) (0353) A mixture of 4-bromo-3-methyl-1H-pyrazole (2 g, 12.5 mmol), 2-iodopropane (6.37 g, 37.5 mmol), Cs2CO3 (6.25 g, 50 mmol) and acetonitrile (30 mL) was stirred at 90 C. for 12 h. The reaction mixture was filtered with MeOH (15 ml) and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (UV214, PE_DMC=100:1 to 50:50) to afford the title compound (700 mg, 56%) as a clear oil. LC-MS: [M+H]+=203.1.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; CHAN, Ho Man; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (134 pag.)US2016/176882; (2016); A1;,
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. 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

18.5 mL of acetic acid is added to 4.1 mL of concentrated sulfuric acid and, while stirring under cooling with ice, 3.85 g (12.1 mmol) of 40% nitrosylsulfuric acid is dropwise added thereto. To the resulting mixture is gradually added 1.71 g (11.0 mmol) of the intermediate (b) (internal temperature: O0C or less), followed by stirring for 2 hours at 0C. 150 mg of urea is added to this reaction solution, followed by stirring for further 15 minutes at O0C to thereby prepare a diazo solution A.

According to the analysis of related databases, 110860-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; WO2009/110643; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 154471-65-5, These common heterocyclic compound, 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole, 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.

Chemical synthesis of compound 16677. For synthesis of compound 16677, 1-methyl-3-trifluoromethyl-5-pyrazolecarboxylic acid 3 (Scheme 1, FIG. 10) was prepared from commercially available compound 1 as previously described (Schlosser et al., (2002) Eur. J. Org. Chem. 2002(17), 2913-2920). Compound 3 (820 mg, 4.2 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (2.0 M in CH2Cl2, 8.5 mmol, 4.2 ml) and a catalytic amount of DMF. The reaction mixture was incubated at room temperature for 5 hours. Evaporation of solvent delivered yellow acyl chloride 4 in quantitative yield.

The synthetic route of 154471-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 3524-32-1, 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 0.5M solution of NaOH in water (100mL) containing aminopyrazole 1 (3mmol, 0.29g) was placed into a glass cell with a cylindrical Ni anode (S=48cm2, activated before the synthesis according to the literature procedure23) and a Ti cathode (S=20cm2). Electrolysis was carried out at a current of 290mA. After passing 2F of electricity per mol of the substrate (Q=579C), the electrolysis was stopped. The reaction mixture was stirred for 0.5h and concentrated HCl was added until the solution was pH ?3. The mixture was then extracted with CHCl3 (3×40mL). The extracts were combined, dried over Na2SO4 and concentrated in vacuo. Column chromatography on silica with light petroleum ether:ethyl acetate (10:1) gave the pure azopyrazole 1a (82%, 0.47g).

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, 5-Amino-1,3-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lyalin, Boris V.; Sigacheva, Vera L.; Kokorekin, Vladimir A.; Petrosyan, Vladimir A.; Tetrahedron Letters; vol. 59; 28; (2018); p. 2741 – 2744;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 175137-46-9, 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. 175137-46-9 name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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 a solution of 1,2,3-trifluoro-4-nitrobenzene (3.2 g, 18 mmol) and DIEA (4.2 ml, 24 mmol) in dry THF (20 ml) was added dropwise the solution of 5-cyclopropyl-lH-pyrazol-3- amine (2.0 g, 16 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 21 hrs. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 5. : 2). Recrystallization from EtOAc (10 ml) and hexanes ((at)100 ml) gave the title compound as red crystals (1.5 g, 33%). NMR (400 MHz) 11.90 (s, 1H), 8.78 (s, 1H), 7.86 (t, J= 7.6 Hz, 1H), 7.08 (q, J= 8.7 Hz, 1H), 5.60 (s, 1H), 1.83 (m, 1H), 0.89 (m, 2 H), 0.65 (m, 2H). MS: Calcd. : 280; Found: [M+H]+ 281.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Cyclopropyl-1H-pyrazol-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics