Tag: M.W:100-200

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. 89179-62-4, name is 1-Methyl-1H-pyrazole-3-carboxamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 89179-62-4

To a solution of 1-methyl-1H-pyrazole-3-carboxamide (400 mg, 3.2 mmol) in dioxane (30mL) was added LAH (365 mg, 9.6 mmol). The resulting mixture was stirred for 3 h at 100°C.After it was cooled to 0°C, it was quenched with 0.4 ml water, 0.4 mL 15percent NaOH aqueous, 1.2mL water in tum. Anhydrous sodium sulfate was added to the solution. The mixture was filteredand concentrated to give the crude product which was used for the next step directly.

The synthetic route of 89179-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; MCCOMAS, Casey C.; REGER, Thomas S.; QI, Changhe; WO2014/139150; (2014); A1;,
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 5334-39-4 as follows. name: 3-Methyl-4-nitro-1H-pyrazole

In analogy to example 6-2, 98.2 mg (0.46 mmol) of a mixture of 4-[(4-amino-3- methyl-1H-pyrazol-1-yl)methyl]benzonitrile and 4-[(4-amino-5-methyl-1H-pyrazol-1- yl)methyl]benzonitrile (intermediate 17C-2 and 18C-2) and 102 mg (0.39 mmol) 6- methyl-2-phenylquinoline-4-carboxylic acid ([CAS-No. 60538-98-9], commercially available at e.g. Enamine, Chemical Diversity Labs, Matrix, Zerenex), were reacted to give after purification using a Biotage chromatography system (25 g snap KP-Sil column, hexane / 50- 100% ethyl acetate, then ethyl acetate / 0- 100% methanol) followed by a separation and purification via preparative HPLC (method 6a) 121 mg (67% yield) of the desired example 41 and 16 mg (9.0% yield) of the desired example 42-2. N-[1-(4-cyanobenzyl)-3-methyl-1H-pyrazol-4-yl]-6-methyl-2-phenylquinoline-4- carboxamide, example 41-2: 1H-NMR (400 MHz, DMSO d6) delta (ppm) = 2.21 (s, 3H), 2.52 (s, 3H), 5.41 (s, 2H), 7.44 (d, 2H), 7.49 – 7.61 (m, 3H), 7.68 (dd, 1H), 7.85 (d, 2H), 7.90 (s, 1H), 8.06 (d, 1H), 8.23 (s, 1H), 8.30 – 8.34 (m, 3H), 8.36 (s, 1H), 10.34 (s, 1H). N-[1-(4-cyanobenzyl)-5-methyl-1H-pyrazol-4-yl]-6-methyl-2-phenylquinoline-4- carboxamide, example 42-2: 1H-NMR (400 MHz, DMSO d6) delta (ppm) = 2.24 (s, 3H), 2.53 (s, 3H), 5.47 (s, 2H), 7.32 (d, 2H), 7.50 – 7.62 (m, 3H), 7.69 (dd, 1H), 7.84 – 7.88 (m, 2H), 7.89 (s, 1H), 7.96 (s, 1H), 8.06 (d, 1H), 8.26 (s, 1H), 8.31 – 8.36 (m, 2H), 10.27 (s, 1H).

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; BUCHMANN, Bernd; CLEVE, Arwed; SIEBENEICHER, Holger; KOPPITZ, Marcus; SCHNEIDER, Dirk; BAUSER, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (482 pag.)WO2016/202898; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

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 chemical industry reduces the impact on the environment during synthesis 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Samar, Chtiba; Fayel, Jemmezi; Jameleddine, Khiari; Tetrahedron Letters; vol. 52; 28; (2011); p. 3648 – 3650;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 14531-55-6, name is 3,5-Dimethyl-4-nitro-1H-pyrazole, molecular formula is C5H7N3O2, 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 C5H7N3O2

6.72 g (47.6 mmol) 3,5-Dimethyl-4-nitro-1H-pyrazole were heated with 7.52 g (57.1 mmol) 3-(chloromethyl)-5-methyl-1,2-oxazole (CAS-No. 35166-37-1) and 8.53 mL (57.1 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene in 25 mL dimethylsulfoxide to 60C overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried, filtered, and evaporated. The crude title compound (10 g) was used without further purification. 1H NMR (400 MHz, DMSO-d6): delta [ppm] = 2.37 (s, 3H), 2.39 (s, 3H), 2.61 (s, 3H), 5.42 (s, 2H), 6.16 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14531-55-6, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; BUCHMANN, Bernd; CLEVE, Arwed; SIEBENEICHER, Holger; KOPPITZ, Marcus; SCHNEIDER, Dirk; BAUSER, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (482 pag.)WO2016/202898; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 20154-03-4, 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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1?3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5?10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C?N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

The chemical industry reduces the impact on the environment during synthesis 3-(Trifluoromethyl)-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
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. 3469-69-0, name is 4-Iodopyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C3H3IN2

(1) Add 19.4 g (0.1 mol) of 4-iodopyrazole, 10.1 g (0.12 mol) of 3,4-dihydro-2H-pyran, and 0.7 g (0.006 mol) of trifluoroacetic acid into the reaction bottle and stir to heat Micro-reflux for 12 hours, the reaction formula of step (1) is as follows:After cooling to room temperature, 0.24 g (0.006 mol) of sodium hydride was added to neutralize the reaction system, and distillation under reduced pressure gave 27.8 g of 4-iodo-1- (tetrahydro-2H-pyran-2-yl) -1H-pyrazole, The product is directly put into the next reaction without purification

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

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; Yang Bing; Zhu Zhiping; Zhang Jianhua; (10 pag.)CN110734401; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 175137-46-9, name is 5-Cyclopropyl-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 175137-46-9, category: pyrazoles-derivatives

To a solution of 2,4-difluoro-l -nitrobenzene (1.76 g, 11.1 mmol) and DIEA (1.93 ml, 11.1 mmol) in TEtaF (20 ml) was added dropwise a solution of 5-cyclopropyl-lH-pyrazol-3- amine (0.91 g, 7.39 mmol) in TEtaF (5 ml) at 25 C. After addition, the reaction mixture was stirred at 80 0C for 48 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : DCM : EtOAc = 2 : 1 : 1) to give the title compound as a yellow solid (0.62 g, 32%). NMR (400 MHz) 12.37 (s, IH), 9.83 (s, IH), 8.25 (m, IH), 7.98 (d, J= 11.2 Hz, IH), 6.75 (m, IH), 5.95 (s, IH), 1.90 (m, IH), 0.96 (m, 2H), 0.72 (m, 2H).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); 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., Recommanded Product: 3994-50-1

Example 25Synthesis of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.A mixture of 0.996 g (8.82 mmol) of 4-nitropyrazole (J. Med. Chem. 2005, 48, 5780-5793) and 1.33 g (10.6 mmol) of dimethyl sulphate in 10 mL of 1 M NaOH was heated at 35 C. for 48 hrs. The reaction mixture was cooled to RT and the precipitate was filtered, washed with water, and dried to give 0.561 g (50% yield) of 1-methyl-4-nitro-1H-pyrazole: 1H NMR (DMSO-d6) delta8.83 (s, 1H), 8.22 (s, 1H), 3.91 (s, 3H).A mixture of 0.144 g (1.14 mmol) 1-methyl-4-nitro-1H-pyrazole, 0.017 g (0.07 mmol) platinum oxide, and ethyl acetate (5 mL) in ethanol (15 mL) was stirred under 2 atmospheres of hydrogen for 14 hrs. The catalyst was removed by filtration through a pad of celite and the solvent was removed to give 0.080 mg (73% yield) of 4-amino-1-methyl-1H-pyrazole as a purple residue, which was used in the next step without further purification: 1H NMR (DMSO-d6) delta6.98 (s, 1H), 6.88 (s, 1H), 3.76 (br s, 2H), 3.65 (s, 3H).A mixture of 0.405 g (4.27 mmol) of 4-amino-1-methylpyrazole and 0.695 g (1.90 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole in DMSO (5 mL) was heated at 125 C. for 15 min. The reaction mixture was cooled to room temperature and water was added. The solid was collected by filtration, washed with water, and dried. Chromatography on alumina, eluting with hexanes/EtOAc (1:1) gave a brown powder. Recrystallization from ethanol/CH2Cl2 gave 0.145 g (18% yield) of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 225-226 C.; 1H NMR (DMSO-d6) (rotamers) delta10.00 (s, 1H), 9.73 (s, 0.2H), 8.60 (d, J=8.0 Hz, 1H), 8.29 (d, J=7.6 Hz, 0.2H), 7.92 (t, JHF=52.8 Hz, 1H), 7.86-7.80 (m, 2.6H), 7.68 (t, JHF=52.6 Hz, 0.2H), 7.59 (s, 1H), 7.52-7.42 (m, 2.9H), 3.85-3.82 (m, 8.4H), 3.75-3.73 (m, 4.8H); Anal. Calcd. for C19H19F2N9O 0.06EtOAc 0.24H2O: C, 52.9; H, 4.6; N, 28.8. Found: C, 52.9; H, 4.5; N, 28.6%.

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; Pathway Therapeutics Limited; US2011/9405; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, 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 5334-39-4, Quality Control of 3-Methyl-4-nitro-1H-pyrazole

A mixture of 3-methyl-4-nitro-lH-pyrazole ( 5 g, 39.34 rnmol), 2-bromoethanoi (9.83 g,78.68 mmol, 5.59 mL) and K2CO3 (16.31 g, 118.02 mmol) in CCN (50 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 80 C for 16 h under N2. The mixture was cooled to 20 C and concentrated under reduced pressure. The residue was poured into ice water (100 mL). The aqueous phase was extracted with EtOAc (3 chi 35 mL). The combined organic phase was washed with brine (35 mL), dried over anhydrous NaaSC^, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 2: 1), to give 2-(5-methyl-4-nitro-pyrazol- 1 -yl)ethanol and 2-(3-methyl-4-nitro-pyrazol-1-yl)ethanol as a yellow oil. LCMS: RT 0.161 min, m/z = 172.2 [M+H]~. -1 NMR (400 MHz, CDC13): delta 8.20 (s, 1 H), 8.03 (s, 1 H), 4.14 – 4.22 (rn, 4 H), 3.94 – 4.03 (m, 4 H), 3.07 (d, 1=5.27 Hz, 2 H), 2.64 (s, 3 H), 2.47 (s, 3 H).To a solution of 2-(5-methyl-4-nitro-pyrazol-l-yl)ethanol (19-2, 4.26 g, 24.89 mmol,), 2-(3-methyl-4-nitro-pyrazol-l-yl)ethanol and Cul (948 mg, 4.98 mmol,) in CH3CN (100 mL) was added a solution of 2,2-difluoro-2-fiuorosulfonyl-acetic acid (6.65 g, 37.34 mmol, 3.87 mL) in CH3CN (10 mL) dropwise at 55 C over a period of 30 min under N2. The reaction mixture was stirred at 55 C for another 2 h. The mixture was cooled to 20 C and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 5: 1 ), to give a mixture of l-[2- (difluoromethoxy)ethyl] -5 -methyl -4-nitro-pyrazole and 1 – [2-(difiuoromethoxy)ethyl -3 -methyl -4-nitro- pyrazole as a yellow oil. LCMS: RT 0.707 min, m/z = 222.1 [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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); 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. 66121-71-9, name is 4-Cyano-1-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Cyano-1-methylpyrazole

Step 3: 5-( 1-methyl-I H-pyrazol-4-yI)-2H-tetrazole1-mcthyl-IH-pyrazole-4-carbonitrile (18 gm, 0.168 moles) obtained instep 2, tn-nbutyl tin chloride (65 gm, 0.218 moles), sodium azide (14 gm, 0.20 Imoles) were taken in toluene (180 ml). The reaction mixture was stirred for 24 hours at 110-120C. The progress of the reaction was monitored by HPLC. The above reaction mixture was cooled to 10-15C, to this added 10% ethanolic HC1 solution (100 ml, pH= 1-2). The reaction mixture was stirred for 1-1.5 hours at 10i5C, filtered off the inorganic salts, washed with ethanol (30 ml). Themother liquor and washings were collected and toluene and ethanol were recovered at 50-55C at reduced pressure. To the abOve residue at 20-25C, added di-isopropyl ether (100ml), stirred for 1-2 hours at 20-25C, filtered the solid, washed with.di-isopropyl ether (30ml) and dried at 60-65C to yield the product, 5-(1-methyl-1H-pyrazol-4-yl)-2H-tetrazole.Drywt 25gmYield 1.4 w/w (99%)

According to the analysis of related databases, 66121-71-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2110; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics