Day: July 9, 2021

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

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

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

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

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

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. 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 179692-08-1

Intermediate 28 (1-28) Ethyl 2-[ 1 -[(tert-butoxycarbonylamino)methyl]-2-[tert-butyl(dimethyl)silyl]oxy-ethyl]- 4-iodo-pyrazole-3-carboxyla Di-tert-butyl azodicarboxylate (1.97 g, 8.53 mmol) was added to a stirred solution of 4- iodo-lH-pyrazole-3-carboxylic acid ethyl ester (1.26 g, 4.74 mmol), [3-(tert- butyldimethylsilanyloxy)-2-hydroxypropyl]carbamic acid tert- vXy ester (2.90 g, 9.48 mmol) and triphenylphosphine (2.24 g, 8.53 mmol) in THF (23.6 mL) under nitrogen atmosphere. The mixture was stirred at rt for 2.5 h. The solvent was evaporated and the residue was treated with DIPE. The solid (Ph3PO) was filtered off and the filtrate was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM in Heptane 50/50 to 100/0 then EtOAc in DCM 0/100 to 3/97). The desired fractions were collected and concentrated in vacuo to yield intermediate compound 1-28 (2.57 g, 98%) as a colorless oil.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN GOOL, Michiel, Luc, Maria; ALONSO-DE DIEGO, Sergio-Alvar; CID-NUNEZ, Jose, Maria; DELGADO-GONZALEZ, Oscar; DECORTE, Annelies, Marie, Antonius; MACDONALD, Gregor, James; MEGENS, Antonius, Adrianus, Hendrikus, Petrus; TRABANCO-SUAREZ, Andres, Avelino; GARCIA-MOLINA, Aranzazu; ANDRES-GIL, Jose, Ignacio; WO2014/195311; (2014); A1;,
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. 866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C12H13N3O2

To a solution of 2,4-dichloro-5-(pyridin-2-yl)benzoic acid (Preparation 30, 3.76 g, 14.02mmol) and ethyl 5-amino-i -phenyl-1H-pyrazole-3-carboxylate (3.89 g, 16.83 mmol) in 2-methyltetrahydrofuran (150 mL) was added DIPEA (7.33 mL, 42 mmol) and the reactionwas heated to 95C. T3P (50% solution in EtOAc, i6.53 mL, 28 mmol) was added andthe reaction was stirred at 95C for i8 hours. The reaction was cooled and partitioned between saturated aqueous sodium carbonate solution (200 mL) and EtOAc (200 mL). The organic layer was collected, washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was triturated with TBME to afford the tftlecompound (5.72 g, 85%).1H NMR (400MHz, DMSO-d6): O ppm 1.33 (t, 3H), 4.35 (q, 2H), 7.03 (s, 1H), 7.47-7.55(m, 4H), 7.61 (d, 2H), 7.72 (d, 2H), 7.75 (5, 1H), 7.98 (t, 1H), 8.74 (d, 1H), 10.88 (1H).LCMS Rt = 3.24 minutes MS mlz 481 [M+H]

The synthetic route of 866837-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAGAL, Sharanjeet Kaur; CUI, Jingrong Jean; GREASLEY, Samantha Elizabeth; LUNNEY, Elizabeth Ann; MCALPINE, Indrawan James; NAGATA, Asako; NINKOVIC, Sacha; OMOTO, Kiyoyuki; SKERRATT, Sarah Elizabeth; STORER, Robert Ian; WARMUS, Joseph Scott; WO2015/170218; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 141573-95-7, 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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

10 g [44.27 mmol, 98.9% GC purity] of 3′,4′,5′-trifluorobiphenyl-2-amine and 9.04 g [44.27 mmol, 99% GC purity] of ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate were dissolved in 35 g of toluene and 7.5 g of NMP. This solution was admixed, under agitation, with 8.37 g of sodium methoxide (30% by weight in methanol) added at 70 C. and 500 mbar in the course of 20 minutes. Methanol and ethanol were removed from the reaction mixture as azeotrope with toluene. On completion of the addition of sodium methoxide the reaction mixture was subsequently stirred at 500 mbar and 70 C. for 15 minutes. The vacuum was then reduced to 300 mbar for 2 hours and to 200 mbar for a further hour. The reaction was tracked via GC-MS analysis to obtain 3-(difluoromethyl)-1-methyl-N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1H-pyrazole-4-carboxamide having a GC-MS purity of 39%.

The synthetic route of Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moradi, Wahed Ahmed; Lui, Norbert; Dockner, Michael; US2014/128617; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 20055-01-0, name is 1-Methyl-1H-pyrazole-4,5-diamine sulfate, 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 20055-01-0, Computed Properties of C4H10N4O4S

To a solution of (2S)-2- [ (BENZYLOXYCARBONYL) AMINO]-5- [ (TERT- butoxycarbonyl) amino] pentanoic acid (22.0 g) and triethylamine (6.7 g) in tetrahydrofuran (240 ml) was added methyl chloroformate (6.2 g) followed by stirring under ice-cooling for 30 minutes. To the reaction mixture was added a solution of 1-METHYL-LH-PYRAZOLE- 4,5-diamine sulfate (12.6 g) and triethylamine (13.4 g) in water (50 ml) at the same temperature. The mixture. was stirred at the room temperature for 1 hour. To the reaction mixture was added chloroform (240 ml), and the layers were separated. The organic layer was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of 1-benzyl 4-tert-butyl { (1S)-1- [ (5-amino-l-methyl-lH-pyrazol-4- yl) carbamoyl] tetramethylene} biscarbamate as an oil. The crude product was used directly in the next step without further purification. A solution of the crude product of 1-benzyl 4- tert-butyl {(LS)-1-[(5-AMINO-1-METHYL-LH-PYRAZOL-4- yl) carbamoyl] tetramethylene} biscarbamate in methanol (200 ml) was treated with 10% palladium on carbon (1.0 g) under a hydrogen atmosphere at room temperature for 6 days. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was triturated with ether and dried in vacuo to give tert-butyl (4S)-4- AMINO-5- [ (5-AMINO-1-METHYL-LH-PYRAZOL-4-YL) AMINO]-5- oxopentylcarbamate (5.5 g) as a solid. 1H-NMR (CDC13) 8 1.40 (9H, s), 1.41 (9H, S), 1.42-1. 44 (4H, m), 2.33-2. 44 (2H, m), 2.85 (3H, s), 3.02-3. 40 (2H, m), 3.38-3. 39 (2H, m), 4.18-4. 20 (1H, m), 4.74 (1H, br), 4.76 (1H, s), 5.24 (1H,. br), 6.39 (1H, d, J = 7 Hz), 7.17 (1H, br), 7.18-7. 30 (15H, m), 7.52 (1H, s)

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-Methyl-1H-pyrazole-4,5-diamine sulfate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; Wakunaga Pharmaceutical Co., Ltd.; WO2005/27909; (2005); 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