Day: June 28, 2021

Adding a certain compound to certain chemical reactions, such as: 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, 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 31230-17-8, Safety of 5-Methyl-1H-pyrazol-3-amine

Step 1: Compound 1a (3.64 g, 20 mmol), 3-amino-5-methyl-pyrazole (1.94 g, 20 mmol) and diisopropylethylamine (5.17 g, 40 mmol) were added to 20 mL of ethanol solution and then stirred at room temperature for 2 days. The insoluble substance was collected to obtain Compound 1b (3.7 g, Yield 76percent), MS [M + 1]+ 244.0.

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-Methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co. Ltd.; DING, Yili; YANG, Xuan; YAN, Qingyan; BAI, Hua; CAI, Lifeng; SMITH, Kenneth; CHAI, Jian; EP2754659; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, 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 127107-23-7, SDS of cas: 127107-23-7

To a 25 mL round-bottom flask containing a solution of intermediate 20.1 (110 mg, 0.27 mmol, 1.00 equiv) in n-Butanol (6 mL) was added 1-methyl- 1H-pyrazol-4-amine hydrochloride (103.2 mg, 0.77 mmol, 2.85 equiv) at room temperature under nitrogen. The reaction was stirred overnight at 110 C in an oil bath. After cooling, the resulting mixture was concentrated under vacuum and resulting crude was purified using flash column chromatography to furnish 120 mg (95%) of compound 1-21 as a yellow solid. LCMS (ES, m/z): 467 [M+H] ?H NMR (400MHz, CDC13): 5 9.02 (1H, s), 7.81 (1H, s), 7.46 (1H, s),7.43 (1H, brs), 4.05-3.93 (1H, m), 3.79 (3H, s), 2.98 (2H, q), 2.53-2.50 (4H, m), 2.39-2.28 (1H, m), 2.05-1.94 (2H, m), 1.85 (2H, d), 1.58-1.30 (8H, m), 1.31 (3H, t), 0.23 (4H,s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazol-4-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna L.; MASSE, Craig E.; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine; WO2015/48281; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

26621-44-3, name is 3-Nitro-1H-pyrazole, 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. COA of Formula: C3H3N3O2

Referential Example 8 5-(Oxetan-3-yl)-lH-pyrazol-3-amine (91) step 1 : Into a 3 L 4-necked round-bottom flask under nitrogen was placed a solution of 3-nitro-lH- pyrazole (100 g, 884.37 mmol, 1.00 equiv.) in THF (1.5 L), followed by the addition of NaH (53 g, 1.32 mol, 1.50 equiv, 60%> suspension) batchwise at 0C. The resulting solution was stirred at 0 C for 1 h. A solution of [2-(chloromethoxy)ethyl]trimethylsilane (1 17.4 g, 704.17 mmol, 1.20 equiv) in THF (500 mL) was then added dropwise with stirring at 0 C. The resulting solution was stirred at 25 C for 1 h, quenched by the addition of EtOH (200 mL), concentrated under vacuum and diluted with 2 L of EtOAc. The resulting mixture was washed with 2×1 L of brine, dried (Na2S04) and concentrated in vacuo. The residue was triturated with 200 mL of petroleum ether. The solids were collected by filtration and washed with petroleum ether (2 x 500 mL) to afford 125 g (52%) of 3-nitro-l -[[2- (trimethylsilyl)ethoxy]methyl]-lH-pyrazole as a yellow solid.

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, A new synthetic method of this compound is introduced below., Quality Control of 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one

General prodedure: NaH (1 mmol) was suspended in DMF (8 mL), then 3-amino-1-phenyl-2-pyrazolin-5-one (1) (0.48 mmol) was dissolved in DMF (10 mL) and added slowly. The mixture was stirred for 30 min at 0 C. Next vinamidinium salt 2 (0.48 mmol) was added and the resulting mixture heated at 80 C for 6 h and the residue partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 and the combined organic layers dried over Na2SO4, filtered and the solvents removed in vacuo. The crude residue was purified by column chromatography (10% EtOAc in hexane) to give products 3a-e. For pyrazolo[3,4-b]pyridine 3f, after evaporation of the solvent, THF (6 mL) and 1 N HCl (6 mL) were added. The mixture was allowed to stir at room temperature for 2 h, then neutralized with saturated aqueous NaHCO3 and extracted with CH2Cl2 (3 × 15 mL). Work-up and purification as above gave 3f.

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; Samar, Chtiba; Fayel, Jemmezi; Jameleddine, Khiari; Tetrahedron Letters; vol. 52; 28; (2011); p. 3648 – 3650;,
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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H6N2O2

Compound 1025; (2R.6S, 12Z, 13aS, 14aR, 16aS)-2-{[7,8-dichloro-2-(propan-2-yloxy)quinolin-4-yl]oxy}- N-[(1-methylcyclopropyl)sulfonyl]-6-{[(1-methyl-1H-pyrazol-3-yl)carbonyl]amino}- 5,16-dioxo-1, 2,3,6,7,8,9,10,11, 13a,14,15,16,16a- tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-; Step V. Coupling with R2a; Macrocydic Brosylate E (1.01 g, 1.26 mmol) is dissolved in 4 N HCI/dioxanes (5 mL) then stirred for 45 mins and concentrated in vacuo. The residue is redissolved in DCM (10 mL), TEA (0.90 mL, 6.5 mmol), TBTU (485 mg, 1.51 mmol) and 1-methyl- 1H-pyrazole-3-carboxylic acid (R2a, 206 mg, 1.64 mmol) are added. The reaction mixture is stirred for 4 h at RT. The reaction mixture is concentrated in vacuo and the resulting material purified by flash chromatography using DCM/MeOH (0 – 10%). The pure fractions are combined and concentrated in vacuo to give intermediate Ga.

The synthetic route of 25016-20-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET, Montse; BORDELEAU , Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63501; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1082745-50-3,Some common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, molecular formula is C9H14N4O2, 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 0.8 g (3.805 mmol) of 5-amino-l-(tetrahydro-pyran-4-yl)-l-H-pyrazole-4- carboxylic acid amide (see PCT patent application WO2010/026214) in 8 mL anhydrous EtOH , 0.457 g (19.6 mmol) of sodium hydride (60 % suspension in mineral oil) were added at room temperature under nitrogen. After 1 h under stirring, 1.2g (11.42mmol) of trans- cyclobutane-l,2-dicarbonitrile were added and the reaction mixture was heated to 140C for 45 min in a microwave oven. The solvent was removed under reduced pressure. The residue was dissolved in DCM, water was added and phases were separated. Organic layers were dried over sodium sulphate and evaporated under reduced pressure. The crude was purified by flash cromatography (Cy/EtOAc from 80/20 to 100%) to obtain the title compound as yellow solid. (0.64g, 55%)HPLC-MS(MethodlEh):R,=6.21minMS (APCI): m/z = 300 (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 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (2012); 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. 63874-99-7, name is 1-(4-Chlorophenyl)-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 63874-99-7

General procedure: 5 mmol 1-Arylpyrazole-4-carbaldehyde, 5 mmol 2-methyl-8-hydroxyl quinoline and 20 mL acetic anhydride were stirred and sealed in a Teflon-lined stainless steel autoclave (25 mL), kept at 160 C for 4 days and then cooled to room temperature. Resultant mixed solution was poured into 100 mL H2O, followed by extractionwith CH2Cl2 (3 50 mL) and rotary evaporation to remove solvent. As-separated crystalline precipitates were dissolved in 25 mL DMF, followed by dropwise addition of 20 mL of aqueous HCl (volume fraction: 36%) at 80 C in a reaction period of 5 h. Then the reactants were allowed to react for additional 4 h after 25 mL of triethylamine was added dropwise. Upon completion of the reaction, the hot mixture was poured into ice water (250 mL) and stirred overnight, followed by extraction with CH2Cl2 (4 100 mL).The combined organic layers were washed with saturated NaCl solution and dried with anhydrous Na2SO4. Crude mixed products were obtained after residual solvent was evaporated under reduced pressure, and as-obtained crude products were purified by column chromatography (silica gel, ethyl acetate/petroleum ether).

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; Ren, Tiegang; Wang, Jie; Li, Guihui; Cheng, Hongbin; Li, Yongzhe; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 129; (2014); p. 7 – 13;,
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. 1572-10-7, name is 3-Amino-5-phenylpyrazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9N3

Compounds8a-e(4.12 g, 20mmol) were dissolved in 30 mL of ethanol followed by the addition of 3-amino-5-phenylpyrazole(3.18 g, 20mmol) and three-four drops ofHCl. Then the reaction mixture was refluxed at ethanol temperature for 2 h. The reaction mixture was allowed to cool to room temperature, and the precipitated product was collected by vacuum filtration and washed with ethanol (3mL) thenrecrystallizedfrom ethanol to afford pure compounds9a-eas yellow solids in good yields.

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; Kamal, Ahmed; Faazil, Shaikh; Hussaini, S.M. Ali; Ramaiah, M. Janaki; Balakrishna; Patel, Nibedita; Pushpavalli; Pal-Bhadra, Manika; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2077 – 2083;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 16617-46-2, These common heterocyclic compound, 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, 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 1. A solution of 5-amino-1H-pyrazole-4-carbonitrile (10 g, 92.51 mmol, 1.00 equiv) in formamide (80 mL) was stirred under nitrogen at 165° C. for 5 h. The reaction mixture was cooled to room temperature and the solid was collected by filtration. The filter cake was washed first with 20 mL of water then 20 mL of methanol and dried to yield 9.5 g (76percent) of 1H-pyrazolo[3,4-d]pyrimidin-4-amine as a white solid.

Statistics shows that 3-Amino-1H-pyrazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 16617-46-2.

Reference:
Patent; Taunton, JR., John William; Brameld, Kenneth Albert; Goldstein, David Michael; Mcfarland, Jesse; Krishnan, Shyam; Choy, Jonathan; US2014/323464; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37687-24-4,Some common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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.

Preparation of Intermediate 1-12.A mixture of Intermediate 1-13 (1.21 g, 2.65 mmol), diethyl 3,5- pyrazoledicarboxylate (539 mg, 2.54 mmol) and K2C03 (440 mg, 3.18 mmol) in acetone (20 mL) was stirred overnight at rt. Water (50 mL) was added and the mixture was extracted with DCM (4 x 150 mL). The combined organic layers were washed with brine (50 mL), dried (MgS04), filtered and evaporated. The residue was purified by column chromatography (EtOAc:cyclohexane, 30:70) and the product obtained was triturated from Et20 to give the desired product (898 mg, 66%) as a white solid.1H N R (300 MHz, DMSO) delta 9.02 (s, 2H), 7.34 (s, 1 H), 7.22 (d, J = 8.6 Hz, 4H), 6.89 (d, J = 8.7 Hz, 4H), 6.14 (s, 2H), 4.83 (s, 4H), 4.31 (q, J = 7.1 Hz, 2H), 4.23 (q, J = 7.1 Hz, 2H), 3.73 (s, 6H), 1.31 (t, J = 7.1 Hz, 3H), 1.22 (t, J = 7.1 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 3,5-pyrazoledicarboxylate, its application will become more common.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALES, Sonia; RODRIGUEZ HERGUETA, Antonio; RAMOS LIMA, Francisco, Javier; ALVAREZ ESCOBAR, Rosa, Maria; HIGUERAS HERNANDEZ, Ana Isabel; WO2011/141713; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics