Day: July 6, 2021

Electric Literature of 82560-12-1,Some common heterocyclic compound, 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, molecular formula is C7H13N3, 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.

Degassed toluene (sparged with argon for 25 mins, 10.0 mL) was added to a mixture of 3-bromo-5-fluorobenzylalcohol (1.00 g, 4.88 mmol), 3-tert-butyl-lH-pyrazole- 5-amine (678 mg, 4.88 mmol), copper (I) iodide (46.0 mg, 0.24 mmol) and potassium carbonate (1.41 g, 10.2 mmol). Trans-N,N’-dimethylcyclohexanediamine (154 mu^, 0.98 mmol) was added and the reaction heated to 150 C for 18 h using microwave irradiation. The mixture was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried (MgS04), filtered and evaporated in vacuo. The residue was purified by FCC, using 0- 100% EtOAc in cyclohexane, to give the title compound (307 mg, 24%). LCMS (Method 4): Rt 2.34 min, m/z 264 [MH+].

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-5-tert-butylpyrazole, its application will become more common.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 121507-34-4, name is 5-Isopropoxy-1H-pyrazol-3-amine, 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 121507-34-4, Safety of 5-Isopropoxy-1H-pyrazol-3-amine

Method 2; 2,5-Dichloro-N-(5-isopropoxy-lH-pyrazol-3-yl)pyrimidin-4-amine; A solution of 2,4,5-trichloropyrimidine (533 mg, 2.93 mmol), 5-isopropoxy-lH- pyrazol-3 -amine (413 mg, 2.93 mmol) and triethylamine (0.49 ml) in TetaF (5 ml) was stirred at room temperature for 10 hours. Solvent was removed and EtOAc was added. The solution was washed with water and dried over anhydrous sodium sulfate and was concentrated to give title compound as a white solid (582 mg, 69%). LC-MS, 246 (M-42); 1H nuMR (CDCl3) delta 8.19 (s, IH), 7.80 (s, IH)5 5.79 (s, IH), 4.65 (m, IH), 1.30 (d, 6H).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/49041; (2007); A1;,
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 56984-32-8 as follows. name: Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate

Example 12; [Show Image] Compound 6 was reacted with various benzylbromides in the presence of cesium carbonate to give Compounds A-26, A-27 and A-28.

According to the analysis of related databases, 56984-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; EP1953145; (2008); 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. 741717-63-5, name is Ethyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 741717-63-5

A mixture of 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (160 mg, 0.56 mmol) and 1N aqueous sodium hydroxide solution (2.3 mL, 2.3 mmol) in methanol (10 mL) was stirred at room temperature overnight. The reaction mixture was acidified to pH2 with 1N aqueous hydrochloric acid and concentrated to give 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid as an off-white solid, which was directly used without further purification. LCMS calcd for C11H7F3N2O (m/e) 256, obsd 257 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 741717-63-5.

Reference:
Patent; Bolin, David Robert; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Hamilton, Matthew Michael; Li, Shiming; McDermott, Lee Apostle; Qian, Yimin; Yun, Weiya; US2007/123504; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 51105-90-9,Some common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, molecular formula is C5H6N2O2, 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.

DIAD (9.39 ml, 43.61 mmol) was added dropwise to an ice-cooled solution of methyl 1 H-pyrazole-4- carboxylate (5 g, 39.65 mmol), tert-butyl (2-hydroxyethyl)carbamate (6.13 ml, 39.65 mmol) and PPrtj (1 1 .44 g, 43.61 mmol) in THF (300 ml). The reaction was then allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was quenchedwith water (150 ml) and the layers separated. The aqueous layer was extracted using EtOAc (3 x 150 ml). The combined organic layers were washed with brine, dried (MgS04), filtered and the solvent evaporated to give the crude product. Purification by flasn column chromatography (eluting with a gradient of 15-100% EtOAc / heptane) gave the title compound (1 1 .3 g, 68%) as a white solid. 1 H-NMR (CDCI3, 500 MHz): d[ppm]= 7.93 (s, 1 H), 7.87 (s, 1 H), 4.25 (t, J = 5.3 Hz, 2H), 3.83 (s, 3H), 3.61- 3.54 (m, 2H), 1.44 (s, 9H) HPLCMS (Method A): [m/z]: 270.1 [M+Hf

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3528-45-8, 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. 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A stirred mixture of triethoxymethane (339 mL, 2037 mmol), and 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum’s acid) (35.2 g, 244 mmol) was heated to 80 C. for 1 hour. A suspension of 1-(4-methoxybenzyl)-1H-pyrazol-5-amine [41.4 g, 204 mmol; prepared according to the procedure described by Misra, R. N., et al. Bioorg. Med. Chem. Lett. 2003, 13, 1133-1136, except desalting was performed as follows: 1-(4-methoxybenzyl)-1H-pyrazol-5-amine hydrochloride (44 g) was partitioned between MTBE (300 mL) and 1N aqueous NaOH (300 mL), after separating the phases, the aqueous suspension was re-extracted with MTBE (8×100 mL), followed by drying (Na2SO4) the combined organic phases, and concentration in vacuo to obtain the free-based 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (30 g)] in triethoxymethane (339 mL, 2037 mmol) was added at once and heating at 80 C. was continued for 18 hours under N2. After cooling to room temperature, toluene azeotrope (2×200 mL) was utilized to remove EtOH. The resulting suspension was diluted with diethyl ether (500 mL) and filtered to obtain a yellow solid (33.5 g, 46%). 1H NMR (400 MHz, CDCl3) delta 11.13 (d, J=13 Hz, 1H), 8.26 (d, J=13 Hz, 1H), 7.50 (d, J=2 Hz, 1H), 7.25 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 6.21 (d, J=2 Hz, 1H), 5.28 (s, 2H), 3.78 (s, 3H), 1.74 (s, 6H).

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

Reference:
Patent; Blake, James F.; Boyd, Steven Armen; De Meese, Jason; Fong, Kin Chiu; Gaudino, John J.; Kaplan, Tomas; Marlow, Allison L.; Seo, Jeongbeob; Thomas, Allen A.; Tian, Hongqi; Cohen, Frederick; Young, Wendy B.; US2007/238726; (2007); 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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, A new synthetic method of this compound is introduced below., Product Details of 3524-32-1

General procedure: In a 50 mL single-mouth flask,Salicylaldehyde (1 mmol) was added in sequence,Ethyl cyanoacetate (1 mmol) and 3-methyl-1-phenyl-5-aminopyrazole (1 mmol),Triethylamine (0.1 mmol) and ethanol (8 mL),The reaction was stirred under reflux for 8 h.After the reaction is over,Cool to room temperature.Rotate the solvent under reduced pressure,Get a rough product,The crude product was recrystallized from 95% ethanol.5-amino-1-methyl-3-phenylcoumarin[4,3-d]pyrazolo[3,4-b]pyridine-6(3H)-one (Ia):Yield 63%

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; Soochow University (Suzhou); Shi Daqing; Zhang Mengye; Xu Wentao; Wang Ning; Huang Zhibin; (17 pag.)CN108409748; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 75415-03-1, These common heterocyclic compound, 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, 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.

Under an argon atmosphere, copper hexahydrate perchlorate [Cu [C104] 2 · 6H20] (167 mg,0.45 mmol) and excess copper powder (230 mg, 3.62 mmol) were stirred in 8 mL of acetonitrile for 20 minutes,After which a solution of 1,4-bis [diphenylphosphine] butane (384 mg, 0.90 mmol) in 12 mL of dichloromethane was added,After stirring for 1 hour, a solution of 3- [2-pyridyl] pyrazole ligand (131 mg, 0.90 mmol) was added,The reaction was continued for 3 hours at room temperature. After filtration, the solvent was evaporated to dryness on a rotary evaporator,And recrystallized from a mixed solvent of dichloromethane (2 mL) and diethyl ether (20 mL) at a volume ratio of 1:10.Filtered and recrystallized to give colorless crystalline product which was washed 3-4 times with 25 mL of diethyl ether,After drying in vacuo, a white solid product was obtained as perchlorate ? bis [3- [2-Pyridyl] pyrazole] bis [mu-Mu-bis [diphenylphosphine] butane] bis [copper (II) complex] (456 mg, 0.31 mmol)was 69%.

The synthetic route of 75415-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi University of Science and Technology; Chen, Jinglin; Guo, Zonghao; He, lihua; Liu, Suijun; Wen, Herui; (13 pag.)CN104877673; (2016); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 103626-03-5, 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. 103626-03-5, name is Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A round bottom flask was charged with starting ethyl 3-hydroxy-1-methyl-4-pyrazolecarboxylate (100 mg, 0.588 mmol). The flask was placed under high vacuum for 5 min, then backfilled with nitrogen atmosphere. DMF (3 mL) was added, followed by sodium hydride (60% dispersion in mineral oil, 27 mg, 1.2 equiv.) at 20 C. The flask was stirred at 20 C. for 60 min, then 4-(2-iodoethyl)morpholine (184 mg, 1.3 equiv.) was added. The reaction was stirred at 80 C. for 16 hr. The reaction was removed from heating and allowed to cool to 20 C., then the reaction was quenched with water and extracted five times into ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 120 mg crude product. Silica gel TLC (95:5 dichloromethane:methanol) of the crude product indicated complete consumption of starting aminopyrazole (Rf ?0.60) and one new UV-active product (Rf 0.50). The resulting residue was dissolved in dichloromethane and purified by flash column chromatography (silica gel, 12 g, 0 to 10% methanol in dichloromethane). The major UV-active product eluted at 5% dichloromethane. Fractions were assayed by silica gel TLC. The fractions containing the major UV-active product were collected and concentrated in vacuo to give ethyl 1-methyl-3-(2-morpholinoethoxy)-1H-pyrazole-4-carboxylate (120 mg). 1H NMR (400 MHz, Chloroform-d) delta 7.63 (s, 1H), 4.37 (t, J=5.7 Hz, 2H), 4.21 (q, J=7.1 Hz, 2H), 3.71 (s, 3H), 3.72-3.69 (m, 4H), 2.82 (t, J=5.7 Hz, 2H), 2.61 (t, J=4.7 Hz, 4H), 1.28 (t, J=7.1 Hz, 3H). LCMS-ESI+ (m/z): [M+H]+ calculated for C13H21N3O4: 284.2; found: 284.1.

The chemical industry reduces the impact on the environment during synthesis Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Gilead Sciences, Inc.; Chu, Hang; Guerrero, Juan A.; Hurtley, Anna E.; Hwang, Tae H.; Jiang, Lan; Kato, Darryl; Kobayashi, Tetsuya; Knox, John E.; Lazerwith, Scott E.; Li, Xiaofen; Lin, David W.; Medley, Jonathan W.; Mitchell, Michael L.; Naduthambi, Devan; Newby, Zachary; Squires, Neil H.; Tsui, Vickie H.; Venkataramani, Chandrasekar; Watkins, William J.; Yang, Hong; (292 pag.)US2019/352271; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, 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. Product Details of 632365-54-9

5-Amino-3-pyrazolcarboxylic acid methyl ester (16.91 g, 119.8 mmol) is dissolved in ethanol (2.4 L) and hydrochloric acid (37%, 12.5 mL, 150 mmol) is added. Then, a solution of 2-bromo-malonealdehyde (18.9 g, 125.2 mmol) is dissolved in ethanol (1.4 L) and is quickly added in a drop wise manner at RT. After 30 min, a precipitation is observed; after 6 hours the precipitate is removed and washed with 50 ml ethanol and thereafter with 50 ml diethyl ether. Here, 4.19 g of the clean product are isolated. After evaporation of the filtrate and crystallisation, additional 1.43 g product are obtained to yield 6-Bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester (5.62 g, 18.3% d. Th.). In case of a smaller scale reaction with only 1 g of the starting amine 5-amino-3-pyrazolcarboxylic acid methyl ester, the yield is much better e.g. 68%.

The synthetic route of 632365-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; US2008/32998; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics