Day: July 12, 2021

Reference of 400755-44-4,Some common heterocyclic compound, 400755-44-4, name is 1-Ethylpyrazole-3-carboxylic Acid, 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.

Example 242 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1-ethyl-1H-pyrazole-3-carboxamide Using 1-ethyl-1H-pyrazole-3-carboxylic acid (128 mg, 0.92 mmol), tetrahydrofuran (2.0 mL), N,N-dimethylformamide (20 muL, 0.26 mmol), oxalyl chloride (80 muL, 0.92 mmol), N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.61 mmol) and N,N-dimethylacetamide (4.0 mL), and in the same manner as in Example 238, the title compound (111 mg, 40%) was obtained as a white powder. 1H-NMR (DMSO-d6, 300 MHz) delta 0.76-0.85 (4H, m), 1.44 (3H, t, J=7.2 Hz), 1.87-1.97 (1H, m), 4.26 (2H, q, J=7.2 Hz), 6.77 (1H, d, J=2.1 Hz), 7.07 (1H, d, J=9.6 Hz), 7.09-7.16 (1H, m), 7.39 (1H, dd, J=11.4, 8.7 Hz), 7.84 (1H, dd, J=6.5, 2.9 Hz), 7.91-7.96 (2H, m), 8.04 (1H, d, J=9.6 Hz), 9.57 (1H, s), 11.07 (1H, s).

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

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); 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. 398491-59-3, name is tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 398491-59-3

A solution of ethyl chlorocarbonate (8. 9 ml, 93 MMOL) in tetrahydrofuran (THF, 250 ml) was slowly added to a mixture of tert-butyl 3-AMINO-4, 6-dihydropyrrolo [3, 4-CPYRAZOLE-5 (1 H)- CARBOXYLATE (20 G, 89 MMOL) and diisopropylethylamine (DIEA, 92 ml, 528 MMOL) in THF (500 ML) at 0-5 C. 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, and the resulting residue extracted with ethyl acetate (AcOEt) and water. The organic layer was separated, dried over sodium sulfate and evaporated to dryness. The mixture was purified by flash-chromatography (eluent : ethyl acetate/cyclohexane 4/6 to 7/3) to give 19 G of the title compound as a white solid. [M+H] + 297

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.; WO2005/5427; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1072-68-0, A common heterocyclic compound, 1072-68-0, name is 1,4-Dimethylpyrazole, molecular formula is C5H8N2, 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.

Sodium hydride (60% dispersion in mineral oil, 0.35 g, 8.65 mmol) was suspended in 12 ml tetrahydrofuran. A solution of 4-methyl-1 H-pyrazole (0.60 g, 7.3 mmol) in 2 ml tetrahydrofuran was added dropwise and the mixture was stirred for 1 h at room temperature. Methyl iodide (0.45 ml, 7.23 mmol) was added drop-wise and the mixture was stirred overnight forming a precipitate. The mixture was filtered and the solid was washed with a little tetrahydrofuran and the filtrates combined to give a crude solution of 1 ,4-dimethyl-1 H-pyrazole. The crude solution was cooled in an ice-bath under nitrogen and n-butyl lithium (1 .6 M in hexanes, 3.70 ml, 5.92 mmol) was added drop-wise with stirring over 15 min. After addition, the mixture was stirred at room temperature for 2 h. The mixture was then cooled to -78 C and a solution of 2-bromo-5-(trifluoromethyl)benzaldehyde (1 .49 g, 5.89 mmol) in 2 ml tetrahydrofuran was added over 1 min. The mixture was stirred overnight, warming to room temperature. The solution was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate. The organic extract was washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified using the Isolera purification system (ethyl acetate-hexanes gradient, 0:100 rising to 100:0) to give 710 mg (2.03 mmol, 41 %) of the title compound as a white solid. Purity 96%. 1H NMR (300 MHz, DMSO-d6) delta ppm 8.13 (d, 1 H, J = 2.3 Hz), 7.86 (d, 1 H, J = 8.2 Hz), 7.66 (dd, 1 H, J = 8.2, 2.3 Hz), 7.08 (s, 1 H), 6.51 (d, 1 H, J = 5.3 Hz), 5.93 (d, 1 H, J = 4.7 Hz), 3.83 (s, 3H), 1.42 (s, 3H). UPLC/MS (3 min) retention time 1 .72 min. LRMS: m/z 349, 351 (M+1 ).

The synthetic route of 1072-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GOMEZ CASTILLO, Elena; GONZALEZ RODRIGUEZ, Jacob; LOZOYA TORIBIO, Maria Estrella; MATASSA, Victor Giulio; MIR CEPEDA, Marta; ROBERTS, Richard Spurring; VIDAL JUAN, Bernat; WO2013/10881; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37718-11-9, name is 1H-Pyrazole-4-carboxylic 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 37718-11-9, Computed Properties of C4H4N2O2

To the stirred solution of lH-pyrazole-4-carboxylic add 19-1 (20 g, 178.43 mmol) in methanol (100 niL) was added H2SO4 (17.50 g, 178.43 mmol, 9.51 rnL) at 0C and the reaction mixture was refluxed for 16 hours at 80C. Solvent was evaporated and the crude material was neutralized by saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate and washed with brine. After separation, the organic layer was dried over sodium sulfate and evaporated to obtain methyl lH-pyrazole-4-earboxylate 19-2 (21 g, 166.52 mmol, 93.32% yield) as white solid. LC MS: ES+127.0.

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; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 51516-67-7, 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. 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

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-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-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: 175137-46-9

The solution of 1,3,5-trifluoro-2-nitrobenzene (6.50 g, 37 mmol), 5-cyclopropyl-1H- pyrazol-3-amine (3.50 g, 28 mmol) and DIEA (6.4 ml, 37 mmol) in THF (100 ml) was stirred at 25 C for 80 hours. The solvent was removed under reduced pressure and the residue was purified by chromatography (DCM-EtOAc = 10 : 1) to give the title compound as yellow solid (4.9 g, 62%). NMR (400 MHz) 12.26 (s, 1H), 9.09 (s, 1H), 7.70 (d, J= 12.8 Hz, 1H), 6.88 (m, 1H), 5.80 (s, 1H), 1.88 (m, 1H), 0.93 (m, 2H), 0.69 (m, 2H).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); 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 75415-03-1 as follows. Safety of 2-(1H-Pyrazol-3-yl)pyridine

A mixture of HL (0.2 mmol, 29 mg), Zn(NO3)26H2O (0.2 mmol, 59 mg),ethanol (1 ml), and H2O (10 ml) was stirred for 0.5 h in air, then the resulting mixture was transferred in a Teflon-linedstainless reactor and heated to 140 C for 3 days under autogenous pressure and cooled to room temperature at a rate of10 C/h. Consequently, the colorless block-shaped crystals suitable for X-ray single crystal diffraction were obtained witha yield of 36.7 % (based on Zn(NO3)26H2O)

According to the analysis of related databases, 75415-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu; Huan; Cui; Han; Journal of Structural Chemistry; vol. 56; 6; (2015); p. 1124 – 1129; Zh. Strukt. Kim.; vol. 56; 6; (2015); p. 1177 – 1182,6;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1222174-92-6, name is Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate, 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 1222174-92-6, COA of Formula: C6H7BrN2O2

Step 2: A solution of the intermediate of step 1 (506 mg, 2.31 mmol) in dioxane (10 mL) was treated withLiOH solution (2 M, 1 mL) and the mixture was stirred at 70 C for 1 h. HCI (1 M) was added and themixture was extracted with EtOAc. The combined organic layers were dried and the volatiles wereremoved under reduced pressure to yield the desired compound (84%).LC-MS (Method 2): mlz [M+Hj = 205.0 (MW calc. = 205.01); R = 0.31 mm.

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, Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; VOSS, Felix; WACHTEN, Sebastian; KLESS, Achim; RITTER, Stefanie; WO2015/90580; (2015); 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. 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. name: 1H-Pyrazole-4-carbaldehyde

In this case, C3 was reacted with 1H-pyrazole-4-carbaldehyde and cesium carbonate to afford tert-butyl 2-(4-formyl-1H-pyrazol-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate. This material was treated with (diethylamino)sulfur trifluoride to provide the requisite tert-butyl 2-[4-(difluoromethyl)-1H-pyrazol-1-yl]-7-azaspiro[3.5]nonane-7-carboxylate.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (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. 4522-35-4, name is 3-Iodo-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H3IN2

1-(chloromethyl)-4-methoxy-benzene (2.10 mL, 15.5 mmol) was added to a stirred mixture of 3-iodo-1H-pyrazole (2.01 g, 10.4 mmol) and Cs2CO3 (6.70 g, 20.6 mmol) in DMF (30.0 mL). The reaction mixture was stirred at 60 C for 2 hours and then, cooled to room temperature. Water (100mL) was added and aqueous was extracted with EtOAc (3 x 50 mL). Combined organic extracts were washed with aqueous saturated NH4Cl (25 mL) solution, brine (25 mL) and dried over MgSO4. The mixture was filtered and concentrated to afford 4.06 g of crude material. The residue was adsorbed on silica using DCM and purified by silica gel chromatography to afford 3-iodo-1-[(4- methoxyphenyl)methyl]pyrazole and 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole (3.18 g, 98%) as a white solid as a ca.5:1 mixture of regioisomers. Major Regioisomer: 1H NMR (400 MHz, CDCl3) 7.23 – 7.15 (m, 3H), 7.12 (d, J = 2.3 Hz, 1H), 6.92 – 6.85 (m, 2H), 6.40 (d, J = 2.3 Hz, 1H), 5.24 (s, 2H). : ESI-MS m/z calc.313.9916, found 314.98 (M+1)+; Retention time: 0.93 minutes Using Method J

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; VERTEX PHARMACEUTICALS INCORPORATED; SAYEGH, Camil Elie; STURINO, Claudio; FOURNIER, Pierre-Andre; LACOSTE, Jean-Eric; DIETRICH, Evelyne; MARTEL, Julien; VALLEE, Frederic; (494 pag.)WO2016/154075; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics