Day: June 2, 2021

Reference of 57999-06-1, 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. 57999-06-1, name is 4-Phenyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of aminoazole 1f-i (1 mmol), acetoacetamides 2a-c (1 mmol), and aromatic aldehyde 3b-f (1 mmol) in 10 mL of ethanol was ultrasonicated at room temperature for 90 min in a round-bottom flask equipped with condenser. The reaction mixture was allowed to stand up to 12 h at room temperature and then was filtered to give the solid compounds 8a-i, which were washed with ethanol and air dried. Reaction products were obtained in high purity and did not require further purification by recrystallization.

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

Reference:
Article; Muravyova, Elena A.; Desenko, Sergey M.; Rudenko, Roman V.; Shishkina, Svetlana V.; Shishkin, Oleg V.; Sen’ko, Yulia V.; Vashchenko, Elena V.; Chebanov, Valentin A.; Tetrahedron; vol. 67; 48; (2011); p. 9389 – 9400;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 10250-64-3,Some common heterocyclic compound, 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, molecular formula is C11H10N2O2, 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: To a solution of 19 (1.2 eq) and HOBt(1.4 eq) in DMF (0.5 M) were added EDCI (1.3 eq) and a solution of 15a-j or 16a-j (1.0 eq) in DMF (0.25 M), Et3N (3.5 eq) at 0 C. The reaction mixture was stirred at room temperature for 24 hours, then diluted in AcOEt. The organic phase was washed with water twice, saturated aqueous NaHCO3 three times, and brine, then dried over Na2SO4,filtered, and concentrated. The residue was purified by flash column chromatography to give intermediates 17a-j and 18a-j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Article; Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 25; 23; (2015); p. 5619 – 5624;,
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. 13745-17-0, name is 4-Bromo-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C4H3BrN2O2

Ste 2: (0585) Preparation of 4-bromo-N-(2,2-dimethoxyethyl)-1H-pyrazole-3-carboxamide: (0586) [00242] To a stirred solution of 4-bromo-1H-pyrazole-3-carboxylic acid (3.4 g, 17.8 mmol) in dichloromethane (100 mL) were added triethylamine (12.42 mL, 89.00 mmol) and 2,2-dimethoxyethanamine (2.9 mL, 26.70 mmol) at room temperature. The reaction mixture was cooled to 0 C and 1-propanephosphonic anhydride solution (T3P) (15.89 mL, 26.70 mmol, 50% in ethyl acetate) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (200 mL) and extract with dichloromethane (3 x 100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound 4-bromo-N-(2,2-dimethoxyethyl)-1H-pyrazole-3- carboxamide (3.6 g, crude) as a white solid. Calculated (M-H): 276.01; Found (M-H): 276.0.

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; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1384973-12-9, name is 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, 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. Recommanded Product: 1384973-12-9

General procedure: A mixture of halide (1 .0 eq.), boronic acid or pinacol ester (1 .5 eq.) and potassium carbonate (2.0 eq.) in 1,4-dioxane and water (3:1, 0.1 M)was degassed by bubbling nitrogen through it for 15 mi 1,1- bis(diphenylphosphino)ferrocene-palladium(ll) dichloride dichloromethane complex (0.05 eq.) was added and the mixture was degassed again by bubbling nitrogen through it for 15 mm. The mixture was then heated under microwave irradiation at 120-140 C for 60-90 mm. The reaction mixture was either purified by SCX SPE cartridge and used as such or purified using the following procedure, unless stated used crude. The mixture was filtered through a pad of Celite. The cake was rinsed with DCM. Water was added to the filtrate and the layers were partitioned. The aqueous layer was extracted with DCM (x2). The combined organic extracts were filtered over phase separator and then concentrated under reduced pressure to give a dark solid. Further purification by flash column chromatography gave the desired compound.; General procedure D, 5-fluoro-N-[[2-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl]methyl]-2-methoxy-benzamide (1 .65 mmol) and 5-amino-3-bromo-1 H-pyrazole-4-carbonitrile (1.34 mmol) gave, after purification, titled compound (0.78 mmol). UPLC-MS (ES, Short acidic): 1.67 mi m/z 384.0 [M+H]

The synthetic route of 1384973-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31230-17-8, The chemical industry reduces the impact on the environment during synthesis 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life.

4,6-dichloro-2- (phenylethynyl) – pyrimidine (0 ? 71 g, 2 · 85 mmol) Wasdissolved DMAC (4 mL) at successively added 3-amino-5-methyl-R than sit Jie (0.31 g, 3. 14 mmol), sodium iodide (0. 51 g, 3. 42 mmol) , DIPEA (0. 6 mL, 3. 42mmol), the mixture was heated to 90 ° overnight with stirring. Ethyl acetate(60 mL) and saturated sodium bicarbonate. The solution (60 mL) was added themixture was extracted, dried, concentrated and purified by column (methylenechloride / methanol (V / V) = 10/1), to give a pale yellow solid (0. 49 g,56percent).

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; GUANGDONG HEC PHARMACEUTICAL CO LTD; ZHANG, YINGJUN; LIU, BING; ZHANG, JIANCUN; ZHANG, JIQUAN; YANG, XUEQI; LI, YANPING; (45 pag.)CN104024246; (2016); B;,
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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Product Details of 31108-57-3

To a stirred solution of ethyl 2-((2-chloroethyl) amino)-2-phenylacetate (0.10 g, 0.413 mmol) in DMF (1 ml) was added K2C03 (0.114 g, 0.827 mmol) at 25 C. After stirring for 15 minutes, 1 /7-pyrazolc-4-carhonitrilc (0.046g, 0.496 mmol) was added at 25 C. The reaction mixture was heated at 60 C for 3 hours. Then the reaction mixture was poured into ice water (15 ml) and the product was extracted with ethyl acetate (2 x 30 ml). The combined organic layers were washed with brine (20 ml), dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound (0.050 g, 40%). LCMS: m/z = 299.76 [M+l].

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; CONSTELLATION PHARMACEUTICALS, INC.; WILSON, Jonathan, E.; BRUCELLE, Francois; LEVELL, Julian, R.; (153 pag.)WO2019/161162; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

The synthetic route of 4-Iodo-1-methyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
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

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: 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