Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 612511-81-6, name is (1-Methyl-1H-pyrazol-3-yl)methanamine, 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 612511-81-6, Product Details of 612511-81-6

To a solution of ethyl 2-(2-amino-4-chloro-6-((l-methyl-lH-pyrazol-3- yl)methylamino)pyrimidin-5-yl)acetate (2.8 g, 8.64 mmol) in n-BuOH (20 mL) was added DIEA (2.5 g, 19.38 mmol). The resulting solution was stirred at 1300C for 12 hr and the solids were collected by filtration, resulted in 2.0 g (83percent) of 2-amino-4-chloro-7-((l -methyl – lH-pyrazol-3-yl)methyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one as a white solid.

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; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 881668-70-8, 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 881668-70-8 as follows.

Add in 100mL round bottom flask5-chloro-1H-pyrazole-3-carboxylic acid (0.122 g, 0.8355 mmol),1.5 mL of anhydrous DMF as a solvent, Add EDCI (0.16 g, 1.0444 mmol), DIPEA (0.24 mL, 1.3926 mmol) and HOBT (32 mg, 0.2089 mmol), Stir for 20 minutes. Add another starting material (S)-3-amino-N-(4-cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methylpropanamide (0.20 g, 0.6963 mmol) a solution of 4.0 mL of anhydrous DMF, Then the reaction solution is under argon protection. Stir at room temperature for 3 days. After confirming the completion of the reaction by thin layer chromatography, ethyl acetate and water were added, the two phases were separated, and the organic phase was drained to obtain Oily substance. Separation by silica gel column chromatography (mobile phase: methylene chloride:methanol = 9:1), purified to give pale yellow powder 0.15 g, the yield was about 51.0%.

According to the analysis of related databases, 881668-70-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yang Guohong; He Junze; Duan Meijuan; (34 pag.)CN108558760; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1572-10-7, name is 3-Amino-5-phenylpyrazole, molecular formula is C9H9N3, 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. COA of Formula: C9H9N3

General procedure: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1572-10-7, its application will become more common.

Reference:
Article; Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin; Chinese Chemical Letters; vol. 31; 2; (2020); p. 418 – 422;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 14531-55-6,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.

General procedure: A mixture of 1.47g (15mmol) of 3,5-dimethylpyrazole, 1.02g (15mmol) of potassium hydroxide, and 10ml of DMSO was stirred at 80C for 1h. A solution of 1.98g (7.5mmol) of 1,4-bis(dibromomethyl)benzene in 10ml of DMSO was added dropwise, the mixture was stirred for 8h at 80C, diluted with 200ml of water, and the precipitate was filtered off ,washed with the mixture of ethanol and water, dried under reduced pressure.

The synthetic route of 14531-55-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Ji-Xiao; Zhu, Zi-Ran; Bai, Feng-Ying; Wang, Xin-Yu; Zhang, Xiao-Xi; Xing, Yong-Heng; Polyhedron; vol. 99; (2015); p. 59 – 70;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 181585-93-3, The chemical industry reduces the impact on the environment during synthesis 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

[00125] delta-Nitro-S-pyrazole-carboxylic acid methyl ester (22.35 g, 130.61 mmol) is dissolved in 160 ml_ THF und 160 ml_ glacial acetic acid. Then, Pd-C (10%, 4.36 g) is added and the reaction is stirred for 6 days under hydrogen atmosphere at RT. Then, the mixture is filtered over celite and the solvent is removed under vacuum. The crude material is dissolved in methylene chloride (800 ml_) and sodium hydrogen carbonate (200 g) is added, filtered and the solvent is again removed under vacuum. This procedure is repeated until the acetic acid smell is lost. delta-Amino-S-pyrazole-carboxylic acid methyl ester is isolated in high yields (16.91 g, 91.7 %)

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, Methyl 5-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints; WO2011/15343; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 176969-34-9, 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. 176969-34-9 name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, 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.

3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (0.211 g, 1.2 mmol) was added to the reaction flask in that order.Dichloromethane (6 ml), N,N-dimethylformamide (2 drops),Add oxalyl chloride (1 g, 8 mmol),The reaction solution was stirred at room temperature for 4 hours. The solvent is then removed by rotary evaporation to give 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid chloride.This was dissolved in dichloromethane (2 mL) for use.Then 4-fluoro-2-(2-pentyloxy)aniline (0.197 g, 1 mmol) was added to the reaction flask and triethylamine (0.13 mL) was added.Further, a solution of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride was added dropwise to the reaction flask, and the mixture was stirred at room temperature for 16 hours.Then after monitoring the reaction by thin layer chromatography,Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.The organic layer was washed with brine and dried over anhydrous sodium sulfate.Obtained 0.298 g of white solid.The yield was 83.94%.

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

Reference:
Patent; Shanghai Taihe International Trade Co., Ltd.; Ma Wenjing; Lv Liang; Li Hongwei; Hou Shuang; Du Yonglei; Liu Jiyong; (31 pag.)CN108383791; (2018); A;,
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. 57012-20-1, name is (1,3-Dimethyl-1H-pyrazol-5-yl)methanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C6H10N2O

2-((l,3-dimethyl-lH-pyrazol-5-yl)methoxy)-5-fluoronicotinic acid (21x)To a solution of 2-chloro-5-fluoronicotinic acid (1.0g, 5.7mmol) in THF (20ml) under a N2 atmosphere was added (l,3-dimethyl-lH-pyrazol-5-yl)methanol (l .Og, 8.0mmol) followed by a portion-wise addition of NaH (60% dispersion in mineral oil, 0.68g, 17mmol). The resulting suspension was stirred at 70C for 16h and then cooled to room temperature and quenched with 1M NaOH (15ml). After washing with DCM (x2), the aqueous layer was acidified with concentrated HC1 until the product precipitated out of solution (~ pH 5). The solids were filtered, washed with ¾0 and then dried under high vacuum to afford the title compound(1.34g, 89%) as a white solid.NMR delta 8.37 (1H, d, J 3.1), 8.02 (1H, dd, J 8.2, 3.1), 6.10 (1H, s), 5.36 (2H, s), 3.75 (3H, s), 2.08 (3H, s);MS (m/e) 266 [M+H]+, Rt 0.71min (QC Method 1)

The synthetic route of 57012-20-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; ASTRAZENECA UK LIMITED; BARNES, Michael, Christopher, Stratton; FLACK, Stephen, Sean; FRASER, Ian; LUMLEY, James, Andrew; PANG, Pui Shan; SPENCER, Keith, Charles; TIBERGHIEN, Nathalie, Anne, Laure; TOMKINSON, Gary, Peter; WO2011/151651; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

292.1 (1H-pyrazol-4-yl)-methanol To a suspension of LiAlH4 (5.3 g) in dry THF (100 mL) in a round-bottomed flask, under inert atmosphere (N2), was added portionwise ethyl pyrazole-4-carboxylate (10.0 g) at rt. The reaction mixture was stirred at rt overnight and then poured into a sat. aq. Rochelle salt solution. The mixture was stirred at rt for 3 h and diluted with EA. The layers were separated and the aq. layer was extracted with EA (3*). The combined org. layers were dried over MgSO4, filtered and concentrated under reduced pressure. The title compound was obtained, after drying, as a white solid (5.2 g; 76% yield). 1H NMR (d6-DMSO) delta: 12.60 (s, 1H); 7.50 (s, 2H); 4.77 (br. s, 1H); 4.38 (br. s, 2H).

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; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37622-90-5,Some common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, molecular formula is C6H8N2O2, 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.

Under anhydrous condition, to a solution of ethyl 4-pyrazolecarboxylate (600 mg) in DMF (21ml, c=0.1 molL-1) cooled by an ice bath, NaH (in mineral oil 60%, 225 mg, 1.3 equiv.) was added in 3 portions (over 5 minutes). The mixture was stirred for 15 minutes, then methyl iodide (410 muL, 1.2 equiv.) was added. The ice bath was removed and the reaction was stirred at room temperature for 1 Hrs. The mixture was hydrolysed with a saturated aqueous solution of NaHCO3 (200 ml) and extracted twice with EtOAc (2*250 ml). The organic layers were combined, washed with brine (400 ml), dried over MgSO4 and concentrated. Purification by flash-chromatography (AcOEt in cyclohexane, 5 to 100%) afforded compound 107 as a colourless oil in 90% yield. 1H-NMR (400 MHz, DMSO): 1.26 (t, J 7.1 Hz, 3H, O-CHrCH3); 1.38 (t, J 7.3 Hz, 3H, N-CHrCH3); 4.17 (q, J 7.3 Hz, 2H, N-CH2-CH3); 4.21 (q, J 7.1 Hz, 2H, O-CH2-CH3); 7.84 (s, 1H, Ar);8.33 (s, 1H, Ar). M/Z (M+H)+ = 169.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-pyrazolecarboxylate, its application will become more common.

Reference:
Patent; DOMAIN THERAPEUTICS; MAYER, Stanislas; SCHANN, Stephan; WO2013/174822; (2013); 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. 4522-35-4, name is 3-Iodo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Iodo-1H-pyrazole

A mixture of 3-iodo-1H-pyrazole (5 g, 25.78 mmol), 3,4-dihydro-2H-pyran (10 g, 118.88 mmol), p-TsOH (900 mg, 5.23 mmol) in tetrahydrofuran (100 mL) was refluxed overnight. The reaction mixture was cooled to room temperature and washed with sat. NaHCO3 (20 mL). The organic layer was separated, dried over Na2SO4, filtered and evaporated. The residue was purified with silica-gel column chromatography (PE:EA=20:1 to 10:1) to give 3-iodo-1-tetrahydropyran-2-yl-pyrazole (7 g, 98% yield) as a light yellow oil. LCMS (ESI) [M+Na]+=300.9. 1H NMR (400 MHz, CDCl3) delta 7.45 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 5.39-5.36 (m, 1H), 4.08-4.04 (m, 1H), 3.72-3.66 (m, 1H), 2.10-2.01 (m, 2H), 1.73-1.54 (m, 4H).

According to the analysis of related databases, 4522-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Daniels, Blake; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Huestis, Malcolm; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Siu, Michael; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Gancia, Emanuela; Jones, Graham; Lainchbury, Michael; Madin, Andrew; Seward, Eileen; Favor, David; Fong, Kin Chiu; Good, Andrew; Hu, Yonghan; Hu, Baihua; Lu, Aijun; US2018/282328; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics