Day: September 22, 2021

Synthetic Route of 15878-00-9,Some common heterocyclic compound, 15878-00-9, name is 4-Chloro-1H-pyrazole, molecular formula is C3H3ClN2, 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 83 trans-4-Chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide Sodium hydride (60% in oil; 57 mg, 1.43 mmol) was added to a solution of 4-chloro-pyrazole (148 mg, 1.43 mmol) in dry DMF (25 mL) under nitrogen at 0 C. in an ice-water bath and the mixture was heated to 40 C. for 1 h. trans-5-Chloro-1-cyclopropyl-1H-pyrazole-4-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (60 mg, 0.18 mmol) was added and the mixture was heated at 110 C. overnight and then cooled. After the DMF was evaporated in vacuo, water and dichloromethane were added. The organic layer was separated, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were concentrated in vacuo and the residue was purified by C-18 reverse phase preparative-HPLC with a gradient of 10-90% acetonitrile/water to give trans-4-chloro-2′-cyclopropyl-2’H-[1,3′]bipyrazolyl-4′-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (56 mg, 77%). LRMS m/z calcd for C20H24ClN5O2 (M+H) 402.2, found 402.2.

The synthetic route of 15878-00-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin William; Fotouhi, Nader; Gillespie, Paul; Goodnow, Robert Alan; Guertin, Kevin Richard; Haynes, Nancy-Ellen; Myers, Michael Paul; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Rossman, Pamela Loreen; Scott, Nathan Robert; Thakkar, Kshitij Chhabilbhai; Tilley, Jefferson Wright; Zhang, Qiang; US2007/225280; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 49633-25-2, name is 3-Isopropylpyrazole, 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. Computed Properties of C6H10N2

Following the procedure of Example 36, Part B, but substituting 3-isopropylpyrazole for 4-bromo-3-isopropylpyrazole, there was prepared 3-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide having a boiling point at 83 C. at 0.03 mm Hg. About 10% of the 5-isopropyl-N,N,alpha-trimethylpyrazole-1-acetamide isomer was present.

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

Reference:
Patent; The Upjohn Company; US3957480; (1976); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-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 176969-34-9, category: pyrazoles-derivatives

To a one-necked flask was added 53.00 g 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid and 72 mL of thionyl chloride,Heating up to the system has a reflow phenomenon,After refluxing for 2 h, the unreacted thionyl chloride was evaporated at atmospheric pressure.System cooling to 60 below, an external anhydrous calcium chloride drying tower,Water pump vacuum distillation of low boiling impurities, get red viscous liquid, placed overnight solidified into white crystals.The yield was 78.25%.

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; Zhejiang Chemical Institute Co., Ltd.; Sinochem Lantian Group Co., Ltd.; Zhu Bingchun; Peng Weili; Yuan Jing; Huang Hongying; Yu Jiping; Wei Youchang; Kong Xiaolin; Chen Jie; (36 pag.)CN106810545; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 175137-46-9, 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. 175137-46-9 name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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.

To a solution of 1,2,3-trifluoro-4-nitrobenzene (3.2 g, 18 mmol) and DIEA (4.2 ml, 24 mmol) in dry THF (20 ml) was added dropwise the solution of 5-cyclopropyl-lH-pyrazol-3- amine (2.0 g, 16 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 21 hrs. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 5. : 2). Recrystallization from EtOAc (10 ml) and hexanes ((at)100 ml) gave the title compound as red crystals (1.5 g, 33%). NMR (400 MHz) 11.90 (s, 1H), 8.78 (s, 1H), 7.86 (t, J= 7.6 Hz, 1H), 7.08 (q, J= 8.7 Hz, 1H), 5.60 (s, 1H), 1.83 (m, 1H), 0.89 (m, 2 H), 0.65 (m, 2H). MS: Calcd. : 280; Found: [M+H]+ 281.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Cyclopropyl-1H-pyrazol-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, 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. Computed Properties of C10H15N3O2

Under argon, the goodsN-Boc-protected pyrazolopyrrolidine (1) (1 eq.) Was mixed in dry acetonitrile and sodium hydride (1.2 eq.) Was added slowly with ice bath cooling. The reaction mixture was stirred for 2 hours at room temperature.The resulting white suspension, iceUnder cooling in the bath, the product trideuteromethanesulfonyl chloride (methanesulfonyl chloride-D3) (2) (2 equivalents) is added slowly.After the addition was completed, the mixture was further stirred at 25 C for 1 hour.LC-MS and TLC showed that the basic reaction of the intermediate was completed.The reaction was quenched by addition of water and extracted with methylene chloride. The organic phases were combined and washed with water.Dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography to give tert-butyl 1- (trideuteromethylsulfonyl) -4,6-dihydropyrrolo [3,4-c] pyrazole- 5 (1H) Ester.

The synthetic route of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Ji Bell Pharmaceutical Co., Ltd.; Zhenjiang Sheng’an Pharmaceutical Co., Ltd.; Geng Zhongyi; Chen Xinghai; (20 pag.)CN107337674; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 3524-32-1, 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 0.5M solution of NaOH in water (100mL) containing aminopyrazole 1 (3mmol, 0.29g) was placed into a glass cell with a cylindrical Ni anode (S=48cm2, activated before the synthesis according to the literature procedure23) and a Ti cathode (S=20cm2). Electrolysis was carried out at a current of 290mA. After passing 2F of electricity per mol of the substrate (Q=579C), the electrolysis was stopped. The reaction mixture was stirred for 0.5h and concentrated HCl was added until the solution was pH ?3. The mixture was then extracted with CHCl3 (3×40mL). The extracts were combined, dried over Na2SO4 and concentrated in vacuo. Column chromatography on silica with light petroleum ether:ethyl acetate (10:1) gave the pure azopyrazole 1a (82%, 0.47g).

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-1,3-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lyalin, Boris V.; Sigacheva, Vera L.; Kokorekin, Vladimir A.; Petrosyan, Vladimir A.; Tetrahedron Letters; vol. 59; 28; (2018); p. 2741 – 2744;,
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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

Synthesis of 257-A and 258-A. A mixture of tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (314 mg, 1.50 mmol), Cs2CO3 (978 mg, 3.00 mmol) and iodomethane (320 mg, 2.25 mmol) in DMF (6 mL) was stirred at room temperature for 16 h. The mixture was diluted with water (18 mL), extracted with EtOAc (10 mL × 3). The combined organic layer was washed with brine (10 mL × 3), dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 50 : 1) to give 257-A and 258-A (270 mg, 81%) as a yellow solid.

According to the analysis of related databases, 1280210-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 154471-65-5, These common heterocyclic compound, 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole, 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.

Chemical synthesis of compound 16677. For synthesis of compound 16677, 1-methyl-3-trifluoromethyl-5-pyrazolecarboxylic acid 3 (Scheme 1, FIG. 10) was prepared from commercially available compound 1 as previously described (Schlosser et al., (2002) Eur. J. Org. Chem. 2002(17), 2913-2920). Compound 3 (820 mg, 4.2 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (2.0 M in CH2Cl2, 8.5 mmol, 4.2 ml) and a catalytic amount of DMF. The reaction mixture was incubated at room temperature for 5 hours. Evaporation of solvent delivered yellow acyl chloride 4 in quantitative yield.

The synthetic route of 154471-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
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. 69843-13-6, name is 1-Methyl-1H-pyrazol-4-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 69843-13-6

Example 4.082- [ [5-Fluoro-2- [(l-methylpyrazol-4-yl)aminol -4-pyridyll amino I -N-methyl-benzamide A mixture of l-methylpyrazol-4-amine (41.7 mg, 0.43 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (41.4 mg, 0.07 mmol), bis(dibenzylideneacetone)palladium (32.7 mg, 0.057 mmol), sodium tert-butoxide (51.5 mg, 0.54 mmol), and 2-[(2-chloro-5-fluoropyridin-4-yl)amino]-N-methylbenzamide (100 mg, 0.36 mmol) was suspended in dioxane (3 mL). The mixture was heated at 150C for 30 minutes in a microwave reactor and then allowed to cool to room temperature. The mixture was loaded onto an SCX column and the product eluted first with MeOH and then with a 7M solution of NH3 in MeOH. Fractions containing product were combined and evaporated. The residue was purified by preparative HPLC and fractions containing product were combined and evaporated to afford example 4.08 (51.2 mg, 42% yield); 1H NMR spectrum: (300 MHz, DMSO) delta 2.78 (3H, d), 3.77 (3H, s), 6.66 – 6.68 (IH, m), 7.07 – 7.10 (IH, m), 7.31 (IH, s), 7.47 – 7.56 (2H, m), 7.69 – 7.72 (IH, m), 7.84 (IH, s), 7.91 – 7.92 (IH, m), 8.51 (IH, s), 8.64 (IH, q), 10.08 (IH, d); Mass spectrum: m/z (ESI+) (M+H)+ = 341.04.

The synthetic route of 69843-13-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/153589; (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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Computed Properties of C4H7N3

(S)-7-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methyl-2H- 1 ,2,3-triazol-4- yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (190 mg, 0.51 mmol), 1-methyl- 1H-pyrazol-5-amine (54.6 mg, 0.56 mmol), cesium carbonate (333 mg, 1.02 mmol) and BrettPhos 3rd generation pre-catalyst (23.16 mg, 0.03 mmol) were suspended in tertbutanol (6mL) and de-gassed for 10 minutes. The reaction was heated to 80 °C for 18hours under nitrogen. Reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (25 mL), dried over sodium sulfate and concentrated in vacuo to give a yellow solid. The crude product was dissolved in DMSO (5 mL), filtered and purified by preparative HPLC (Waters XBridge Prep C18 OBD column, Sji silica, 30 mm diameter, 100 mm length),using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents.Fractions containing the desired compound were evaporated to dryness to afford (S)-3-methyl-7-(5 -methyl-2-(( 1-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methyl-2H- 1,2,3 -triazol-4-yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (102 mg, 46.2percent) as a white solid. ?H NMR (500 MHz, DMSO, 30 °C) 1.15 (3H, d), 2.33 (3H, s), 3.70(3H, s), 3.9 – 4.01 (1H, m), 4.12 (3H, d), 4.14 – 4.32 (2H, m), 4.35 (1H, d), 5.08 (1H, d),6.27 (1H, d), 7.26 (1H, d), 7.34 (1H, d), 7.64 (1H, d), 7.69 (1H, s), 8.24 (1H, s), 9.08 (1H,s). mlz: ES+ [M+H]+ = 433.

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; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics