Tag: M.W:200-300

Synthetic Route of 916766-83-1, A common heterocyclic compound, 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, molecular formula is C11H11ClN2, 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.

To a mixture of 3- ( (3S, 4S) -4-hydroxytetrahydro-2H-pyran-3-yl) -7, 8-dimethyl-6- (4,4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-2- yl) -2H-benzo [e] [1, 3] oxazin-4 (3H) -one (0.06 g), 3-(4- (chloromethyl) phenyl) -1-methyl-lH-pyrazole (0.03 g) and 2 M aqueous sodium carbonate solution (0.16 mL) in DME (3 mL) -water (0.3 mL) was added 1, 1′ -bis (diphenylphosphino) ferrocenepalladium (II) chloride (0.01 g) , and the mixture was subjected to microwave irradiation at 110C for 50 min. The. reaction mixture was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue waspurified by NH silica gel column chromatography (ethylacetate/hexane) and solidified with ethanol to give the title compound (0.02 g) .XH NMR (300 MHz, DMSO-d6) delta 1.39-1.60 (1H, m) , 1.83-1.97 (1H, m) , 2.11 (3H, s), 2.16 (3H, s) , 3.33-3.54 (2H, m) , 3.64-3.74 (1H, m) , 3.86 (6H, s) , 4.00 (2H, s) , 5.06 (1H, d, J = 5.3 Hz) , 5.20-5.40 (2H, m) , 6.61 (1H, d, J = 2.1 Hz), 7.12 (2H, d, J = 8.3 Hz), 7.46 (1H, s) , 7.63-7.73 (3H, m) .

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; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); 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 6647-93-4 as follows. category: pyrazoles-derivatives

A suspension of 4-iodo- 1 H-pyrazole-3-carboxylic acid Compound la(500 mg, 2.101 mmol), 4-methoxy-benzene-l ,2-diamine dihydrochloride (443 mg, 2.101 mmol), HATU (799 mg, 2.101 mmol), and diisopropyl ethylamine (815 mg, 6.303 mmol) in 15 ml DMF was stirred at 50 C for 16 hrs. After cooled to rt, the mixture was diluted with 150 ml EtOAc, washed with water (7 times) and brine, then dried with Na2SO4. Evaporation give 4-iodo- 1 H-pyrazole-3-carboxylic acid (2-amino-5-methoxy-phenyl)-amide Compound Ib (615 mg, 81.7 %) as a yellowish powder. NMR (DMSO): delta 3.70 (s, 3H), 6.20 (m, IH), 6.46 (s, H), 7.12 (d, J=8.0 Hz, IH), 8.10 (s, IH). MS m/z 358 (MH+).

According to the analysis of related databases, 6647-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/48502; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 54006-63-2, 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. 54006-63-2, name is 5-(4-Chlorophenyl)-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To amixture of 3-(3-chlorophenyl)-1H-pyrazole-5-carboxylic acid (14a, 133 mg, 0.60 mmol) inDMF(4 mL)was added (S)-methyl-4-(2-amino-3-phenylpropanamido)benzoate hydrochloride (12, 200 mg,0.60 mmol), N,N-diisopropyl-ethylamine (232 mg, 1.80 mmol), 1-hydroxybenzotriazole(161 mg,1.20 mmol) and N-(3-dimethylaminopropyl)-N0-ethylcarbodiimide hydrochloride (229 mg, 1.20 mmol)and the reaction mixture was stirred at room temperature overnight.Then TLC analysis indicatedreaction was complete, and H2O (40 mL) was added.The mixture was stirred for 10 min and filtered toget crude product 13a as a yellow solid, which was used for next step without further purification.

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-(4-Chlorophenyl)-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wei, Qunchao; Zheng, Zhichao; Zhang, Shijun; Zheng, Xuemin; Meng, Fancui; Yuan, Jing; Xu, Yongnan; Huang, Changjiang; Molecules; vol. 23; 8; (2018);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

75092-30-7, name is 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, 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. Safety of 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid

Step 1. 4-[(4-Benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 8.0 g, 31.74 mmol), 4-benzylaniline (21.03 g, 114.76 mmol) and copper powder (3.2 g) in a mixture of 5% aqueous sodium carbonate (160 ml) and dimethylsulfoxide (80 ml) was stirred for 17 h at 100 C. After cooling to room temperature, the mixture was filtered through a pad of Celite, which was washed with water, 2N aqueous sodium hydroxide and diethyl ether. The separated water layer was washed with diethyl ether (100 ml*2). The water layer was acidified with concentrated hydrochloric acid and the formed solid was collected by filtration, dried, to give 4.86 g (50%) of the pure title compound as a pale brown solid. Rf value: 0.50 (methanol/dichloromethane/acetic acid=1/10/2 drops). 1H-NMR (DMSO-d6) delta: 7.63 (1 H, s), 7.50 (1 H, br s), 7.31-6.96 (9 H, m), 4.00 (3 H, s), 3.85 (2 H, s). One signal was not observed.

The synthetic route of 75092-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kawamura, Kiyoshi; Mihara, Sachiko; Nukui, Seiji; Uchida, Chikara; US2003/130277; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 73387-52-7, name is 5-(4-Bromophenyl)-1-methyl-1H-pyrazole, 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 73387-52-7, Safety of 5-(4-Bromophenyl)-1-methyl-1H-pyrazole

Step 4: Preparation of 4-(3-{[4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio]phenyl) tetrahydro-2H-pyran-4-carboxamide; Scale-Up Alternative; 4-{3-[(tri-isopropylsilyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide (200 g, 0.51 moles), 5-(4-bromophenyl)-1-methyl-1H-pyrazole (126 g, 0.53 moles), and 2-methyltetrahydrofuran (2,000 mL, 10 mL/g of tips carboxamide) were put into the reactor and sparged with nitrogen while heating to 60 C. The sodium methoxide (244.0 mL, 1.07 moles, added as sodium methoxide in methanol solution 25% w/w) was added to the reactor and sparging was continued for another 30 minutes. PdCl2DPPF (3.7 g, 0.005 moles) was added to the reactor and the mixture was heated to 70 C. Once the amount of tips carboxamide was less than 1% of starting amount, the mixture was cooled to 0 C. The mixture was held at 0 C. for one hour. The mixture was filtered and the solid was washed with 2-methyltetrahydrofuran (3×2.5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor and triturated with water (2,000 mL, 10 mL/g) for two hours at 20 C. The mixture was filtered and the solid was washed with water (2,000 mL, 2×5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor with the Si-thiol (90.0 g, 0.5 g/g) and THF (about 12.8 L, 70 mL/g). The mixture was heated to 60-65 C. and held for two hours. The mixture was cooled to 25 C. and filtered. The Si-thiol was washed with THF (about 0.9 L, 5 mL/g). The solution was distilled to a concentration of 10 mL/g. The mixture was cooled to 25 C. and hexanes (422.5 mL, 5 mL/g) was added. The mixture was filtered and the solid was washed with hexanes (422.5 mL, 5 mL/g). The solid was dried in a vacuum oven at 70 C.For 2-methyltetrahydrofuran and water, mL/g are referred to grams of tips carboxamide. For Si-thiol, tetrahydrofuran and hexanes, mL/g are referred to grams of title compound.

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; Graneto, Mathew J.; Maddux, Todd M.; Masferrer, Jaime L.; US2008/125474; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 575452-22-1, name is 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole, molecular formula is C7H11IN2O, 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: C7H11IN2O

General procedure: To a suspension of magnesium (1.3 equiv) in THF (for 1 mol of magnesium 700 mL of THF wereused), at the boiling temperature under argon atmosphere, ethyl bromide (1.4 equiv) was addeddropwise and left to stir at same temperature for one hour. Then the reaction mixture was cooleddown to given temperature and solution of starting pyrazole derivative 2a, 3a or 6a (1 equiv) inTHF (for 1 mol of pyrazole 350 mL of THF were used) was added dropwise at same temperature.After 1 hour of stirring at the same temperature dimethylformamide (1.5 equiv) was added to thereaction mixture dropwise and left to warm to room temperature overnight. Then saturated NH4Cl(5 equiv) solution in deionized water were added to the reaction mixture, organic layer wasseparated and NH4Cl solution was extracted with dichloromethane (for 1 mol of pyrazole 0.5 L ofdichloromethane were used) twice. Organic layers were combined, washed with deionized water(for 1 mol of pyrazole 0.5 L of water were used), dried with anhydrous Na2SO4 and evaporatedunder reduced pressure. Products were purified by distillation or column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 575452-22-1, its application will become more common.

Reference:
Article; Mazeikaite, Rita; Sudzius, Jurgis; Urbelis, Gintaras; Labanauskas, Linas; ARKIVOC; vol. 2014; 6; (2014); p. 54 – 71;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 15001-11-3, 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 15001-11-3 as follows.

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

According to the analysis of related databases, 15001-11-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 15001-11-3, These common heterocyclic compound, 15001-11-3, name is Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-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.

General procedure: To ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate (2a, 1.60 g, 6.92 mmol) in 4N HCl in 1,4-dioxane (35 mL) at room temperature was added methyl cyanoformate (1.77 g, 20.8 mmol). The mixture was stirred at 100 C for 14 h and was cooled to room temperature. After 1,4-dioxane was removed in vacuo and the residue was partitioned between methylene chloride and water. The organic layer was dried over magnesium sulfate and was evaporated in vacuo. The residue was chromatographed on a silica gel column with a mixture of methylene chloride and ethyl acetate (7:1) to give the desired product 3a (1.47 g, 78 %).

The synthetic route of 15001-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Heo, Yun-Jeong; Jeon, Moon-Kook; Tetrahedron; vol. 73; 40; (2017); p. 5959 – 5973;,
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. 105994-77-2, name is 4-Bromo-1-methyl-5-phenyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Bromo-1-methyl-5-phenyl-1H-pyrazole

General procedure: A mixture of 5.17 g of 4-chloro-1-ethyl-6-nitroquinolin-2(1H)-one, 4.26 g of cyclopropylboric acid monohydrate, 10.9 g of sodium carbonate, 0.44 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 50 mL of ethylene glycol dimethyl ether, and 5.0 mL of water was heated to reflux under a nitrogen atmosphere for 3 hours. Thereafter, the reaction mixture was cooled to room temperature, and ethyl acetate and water were then added thereto. An organic layer was separated, was then successively washed with water and a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. Diisopropyl ether, ethyl acetate and hexane were added to the obtained residue, and a solid was collected by filtration and was then washed with diisopropyl ether to obtain 4.81 g of 4-cyclopropyl-1-ethyl-6-nitroquinolin-2(1H)-one in the form of a slightly brown solid. 1H-NMR (CDCl3): 0.79-0.87 (2H, m), 1.15-1.24 (2H, m), 1.37 (3H, t, J=7.3 Hz), 2.11-2.23 (1H, m), 4.37 (2H, q, J=7. Hz), 6.54 (1H, s), 7.47 (1H, d, J=9.2 Hz), 8.42 (1H, dd, J=9.2, 2.6 Hz), 9.00 (1H, d, J=2.6 Hz).

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; FUJIFILM Corporation; FUJIFILM Toyama Chemical Co., Ltd.; NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY; MAKITA, Keiko; SAEKI, Kazunori; TANAKA, Tadashi; FUJINO, Masataka; NATSUME, Tohru; FURUYA, Kentaro; (120 pag.)US2019/314360; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 54006-63-2, 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. 54006-63-2, name is 5-(4-Chlorophenyl)-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Acid 68 (0.898 mmol), HOBt (0.898 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.898 mmol) were dissolved in CH2Cl2 (5 mL) and stirred for 10 min. EDC (0.898 mmol) in 5 mL of CH2Cl2 was added dropwise over 20 mins in which the colorless reaction mixture was stirred for 48 hrs. at room temperature under nitrogen. The reaction mixture was diluted with 10 mL of CH2Cl2, washed 2 times with water and twice with brine. The organic layer was dried with Na2SO4 and concentrated to give the amide 69 as a light yellow solid, which was used in the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis 5-(4-Chlorophenyl)-1H-pyrazole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Burnham Institute; US2010/16292; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics