Tag: M.W:100-200

These common heterocyclic compound, 1621-91-6, name is 1H-Pyrazole-3-carboxylic acid, 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. Formula: C4H4N2O2

Dimethyl sulfate (236 g, 177 mL, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20% aqueous sodium hydroxide (850 mL) at 40 C. The reaction mixture was heated at 80 C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HCI, the precipitate filtered, washed with water, and dried under vacuum to yield 1-methylpyrazole-5-carboxylic acid (85 g, 38%). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid.

The synthetic route of 1H-Pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58702; (2004); 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 2075-45-8 as follows. name: 4-Bromo-1H-pyrazole

Step 1 : 4-(Methylthio)-1H-pyrazole A suspension of 4-bromopyrazole (4 g, 27 mmol) in tetrahydrofuran (68 mL) was cooled to 0C and n-butyllithium (2.5 M in hexanes, 35.9 mL, 90 mmol) was added dropwise over a period of 20 min. The reaction mixture was stirred at room temperature for 1 h and then was cooled to 0C. 1 ,2-Dimethyldisulfide (2.66 mL, 30.0 mmol) was added dropwise. The reaction mixture was stirred at 0C for 1.5 h. The reaction mixture was poured into water (150 mL) and then it was acidified to pH~8 with a saturated aqueous solution of ammonium chloride and a solution of aqueous hydrochloric acid (1 N). The mixture was extracted with ethyl acetate (150 mL x 3) and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 4-(methylthio)-1 H-pyrazole (3300 mg). 1H NMR (500 MHz, CDCI3) delta 2.36 (s, 3H), 7.63 (s, 2H).

According to the analysis of related databases, 2075-45-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; AHN, Kay; BOEHM, Markus; CABRAL, Shawn; CARPINO, Philip A.; FUTATSUGI, Kentaro; HEPWORTH, David; KUNG, Daniel W.; ORR, Suvi; WANG, Jian; WO2013/150416; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 876343-24-7, The chemical industry reduces the impact on the environment during synthesis 876343-24-7, name is 1-Ethyl-1H-pyrazol-4-amine, I believe this compound will play a more active role in future production and life.

Example 1; iV-(l-ethyl-lJ-pyrazol-4-yl)-2-[2-methoxy-4-(l,6-naphthyridin-4-yloxy)phenyl]acetamide; Diisopropylethylamine (0.417 ml) and 2-(7-azabenzotriazol-l-yl)- 1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.395 g) were added in turn to a stirred mixture of 2-[2-methoxy-4-(l,6-naphthyridin-4-yloxy)phenyl]acetic acid (0.27 g),4-amino-l -ethyl- 1/i-pyrazole (0.179 g) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The resultant mixture was evaporated and the residue was purified by reversed-phase preparative HPLC on a Waters ‘Xbridge’ Cl 8 column (5 microns silica, 19 mm diameter, 100 mm length) using a solvent gradient comprising 13:17 to 100:0 mixtures of acetonitrile and 0.02M aqueous ammonium carbonate as eluent for 4.5 minutes at a flow rate of 40 ml per minute. The material so obtained was further purified by column chromatography on silica using a solvent gradient from methylene chloride to a 9:1 mixture of methylene chloride and 7M methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.12 g); 1H NMR Spectrum: (DMSOd6) 1.33 (t, 3H), 3.61 (s, 2H), 3.77 (s, 3H), 4.07 (q, 2H), 6.75 (d, IH), 6.91 (m, IH), 7.06 (d, IH), 7.37 (d, IH), 7.42 (s, IH), 7.88 (s, IH), 7.92 (d, IH), 8.82 (d, IH), 8.9 (d, IH), 9.71 (s, IH), 10.05 (s, IH); Mass Spectrum: M+H+404.

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, 1-Ethyl-1H-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); 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. 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(Trifluoromethyl)-1H-pyrazole

To a solution of 2-fluoro-3-hydroxybenzonitrile (0.92 g, 6.7 mmol) and4-(trifluoromethyl)-JH-pyrazole (1.0 g, 7.3 mmol) dissolved in 14 mL ofN,N-dimethylacetamide under a nitrogen atmosphere was added powdered potassium carbonate (2.78 g, 20.1 mmol). The resulting mixture was then heated at 153 C for 18 h. The cooled reaction mixture was diluted with de-ionized water and ethyl acetate and the layers separated. The aqueous layer was extracted (4X) with ethyl acetate, and the combined organic layers were washed (3X) with de-ionized water followed by brine. The combinedorganic layers were dried over Mg504, filtered and concentrated to give 1.58 g of an oil. Chromatography through 40 g of silica gel eluting with a gradient of 20 to 40% ethyl acetate in hexanes to give 1.37 g of a solid. The solid was filtered from hexanes to give 680 mg of the title compound.1H NMR oe 9.86 (bs, 1H), 8.64 (s, 1H), 8.07 (s, 1H), 7.40 (m, 2H), 7.37 (m, 1H).

According to the analysis of related databases, 52222-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; SHARPE, Paula Louise; STEVENSON, Thomas Martin; DEPREZ, Nicholas Ryan; REDDY, Ravisekhara P.; CHITTABOINA, Srinivas; WO2015/89003; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 4149-06-8,Some common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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.

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, its application will become more common.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37622-90-5, 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. 37622-90-5 name is Ethyl 4-pyrazolecarboxylate, 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.

Intermediate 8 -(4-Chloromethyl-benzyl)-1 H-pyrazole-4-carboxylic acid ethyl ester 1 H-Pyrazole-4-carboxylic acid ethyl ester (2 g, 13.9 mmol), (4-chloromethyl-phenyl)- methanol (2.21 g, 13.9 mmol) and triphenylphosphine (4.49 g, 16.8 mmol) are dissolved in tetrahydrofuran (40 ml). The solution is cooled to 0C then diethylazodicarboxylate(6.47 ml, 16.6 mmol) is added. The mixture is stirred at 0C for 2 hours, then 1 hour at room temperature. The solvent is removed under vacuum and the residue is purified by flash chromatography (0 – 50% ethyl acetate in cyclohexane) to give the title compound (Yield 1 .72 g). LC (Method 2): tR = 4.40 min; Mass spectrum (ES+): m/z = 279 [M+H ]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-pyrazolecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (92 pag.)WO2017/72020; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 114474-28-1, 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. 114474-28-1 name is 4-(1H-Pyrazol-4-yl)aniline, 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.

[0255] A mixture of 2,4-dichloropyrido[3,4-d]pyrimidine (250 mg, 1.25 mmol), 4-(lH- pyrazol-4-yl)aniline (199, 1.25 mmol), and iPr2NEt (0.44 mL, 2.50 mmol) in DMF (2.5 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (400 mg, 99%). MS (ES+) m/e 323 (M+H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1H-Pyrazol-4-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; KIM, Ji-In; POYUROVSKY, Masha; LIU, Kevin; BARSOTTI, Anthony; MORRIS, Koi; (344 pag.)WO2016/210330; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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 4149-06-8, SDS of cas: 4149-06-8

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(4-(Chloromethyl)phenyl)-1H-pyrazole

N-(trans-2-hydroxycyclohexyl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide (224 mg), 1-[4-(chloromethyl)phenyl]-1H-pyrazole (125 mg), tripotassium phosphate trihydrate (330 mg) and Pd(dppf)Cl2 DCM (25.0 mg) were stirred in a mixed solution of 1,4-dioxane (10 mL) and water (1 mL) under a nitrogen atmosphere at 80C for 16 hr. To the reaction mixture was added ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (49.0 mg).

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; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, 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 660845-30-7, SDS of cas: 660845-30-7

In a 500 ml flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carbaldehyde are added to 30 ml of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 ml of water is added to the reaction mixture, followed by 103 ml of a 30% solution of hydrogen peroxide in water, whilst keeping the temperature below 37 C. After the end of the addition, the reaction mixture is stirred at 50 C for 7 hours. Once the reaction mixture is back to room temperature, the two phases are separated and the organic phase is extracted with 100 ml of water. The combined aqueous phases are acidified to pH 2 with aqueous hydrochloric acid. The resulting white precipitate is filtered, washed twice with 20 ml of water, and dried to yield 3.2 g of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxylic acid as a white solid. H NMR (400 MHz, DMSO-c/6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1 H, JHF = 53.60 Hz)13.19 (s, 1 H); IR (KBr) : 1688 cm”1 (C=0); 2200-3200 cm”1 broad (hydrogen bond).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; DAHMEN, Peter; DESBORDES, Philippe; GARY, Stephanie; HADANO, Hiroyuki; VORS, Jean-Pierre; WACHENDORFF-NEUMANN, Ulrike; WO2012/52491; (2012); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics