Day: September 18, 2021

Adding a certain compound to certain chemical reactions, such as: 398495-65-3, name is 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, 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 398495-65-3, HPLC of Formula: C13H20N4O4

General procedure: To a solution of 2 (13.00 g, 43.90 mmol) and DIEA ( 33.60 g, 260.00 mmol) in dry THF (400 mL) was added dropwise a solution of corresponding acyl chlorides (48.30 mmol) in dry THF (50 mL) over a period of 1 h at room temperature. The reaction mixture was stirred for 12 h at the same temperature and concentrated under reduced pressure. The residue was treated with ethyl acetate / saturated saline (400 mL: 400 mL) and stayed for 2 h, and then filtered. The precipitate was washed with diethyl ether (30 mL), and dried in vacuo to yield the title compounds 3a-d. 3e was obtained by flash chromatography (180 g silica gel, petroleum ether/AcOEt, 0-30%, V/V).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Bai, Xiao-Guang; Yu, Dong-Ke; Wang, Ju-Xian; Zhang, Hao; He, Hong-Wei; Shao, Rong-Guang; Wang, Yu-Cheng; Li, Xue-Mei; Bioorganic and medicinal chemistry letters; vol. 22; 22; (2012); p. 6947 – 6951,5;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 82231-58-1, These common heterocyclic compound, 82231-58-1, name is Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate, 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.

Step 3: Ethyl [4-(2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidin-5-yl)-1H-pyrazol-1-yl]acetateInto a 50-mL round-bottom flask equipped with a magnetic stirbar and reflux condenser was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidine (311 mg, 1.35 mmol), ethyl (4-bromo-1H-pyrazol-1-yl)acetate (400 mg, 0.89 mmol), PdCl2(dppf) (36 mg, 0.05 mmol), 2 M aqueous sodium carbonate solution (0.89 mL, 1.8 mmol) and DMF (4 mL). The resulting suspension was degassed under nitrogen for 20 min and then heated in the microwave to 120 C. for 20 min. The mixture was poured into a 125-mL separatory funnel containing a saturated aqueous KH2PO4 solution (50 mL) and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification by column chromatography through silica gel, eluting with 30% EtOAc in hexanes to 70% EtOAc in hexanes as a gradient gave the title compound as a white solid. MS (ESI, Q+) m/z 476 (M+1).

Statistics shows that Ethyl 2-(4-bromo-1H-pyrazol-1-yl)acetate is playing an increasingly important role. we look forward to future research findings about 82231-58-1.

Reference:
Patent; Leblanc, Yves; Powell, David; Ramtohul, Yeeman K.; Leger, Serge; US2008/182838; (2008); 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. 943541-20-6, name is 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H7ClN4

1.4 A suspension of 3.89 g (20.0 mmol) of 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine and 4.58 g (20.0 mmol) of (3-bromophenyl)acetohydrazide in 40 ml of 1-butanol is heated at 130 C. for 18 hours. The reaction mixture is cooled and partitioned between ethyl acetate and saturated sodium hydrogencarbonate solution. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane /tert-butyl methyl ether /methanol as eluent: 3-(3-bromobenzyl)-6-(1-methyl-1H-pyrazol-4-yl)-1,2,4-triazolo-[4,3-b]pyridazine as beige crystals; ESI 369, 371.

The synthetic route of 943541-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/92498; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2458-26-6, 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. 2458-26-6 name is 3-Phenyl-1H-pyrazole, 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 3-phenyl-1H-pyrazole (188mg, 1.3mmol) in DMF (8mL) was added NaH (60% in oil, 60mg, 1.5mmol) and the solution was stirred for 5min. To the solution was added compound 78a (200mg, 1.Ommol) and the solution was heated to 6O0C for 1h. Allowed to cool, concentrated under vacuum, and purified by preparative TLC (30%EtOAc/hexanes) to yield compound 78b(61 mg, 20%).

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

Reference:
Patent; SCHERING CORPORATION; WO2009/111442; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 187998-35-2, name is 1-(4-Chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid, 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 C11H9ClN2O2

(3) Reference Example 1 [(trifluoromethyl) pyridin-5-yl] (3) 5-methyl-1 in -1H- pyrazole-4-carboxylic acid in place of Reference Example 6 in 1 – (4-chlorophenyl) -5-methyl -1H- pyrazole-4-carboxylic acid, the reaction process using the same acid under ice-cooling and the reaction mixture (281mg) by 1- (5-amino-3-cyano It was added to a pyridine solution of the no-2-yl) -4-cyano nopi piperidine (228mg) and, after stirring 0.25 hours at the same temperature, tri ethyl amine was added, was stirred at room temperature for 2 hours. After the reaction, water was added, and the precipitated solid was collected and then filtered, washed by suspension to give the title compound (425mg) as a white solid

The synthetic route of 1-(4-Chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 5932-27-4, The chemical industry reduces the impact on the environment during synthesis 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

1H-pyrazole-3-carboxylic acid ethyl ester (5.00 g, 35.7 mmol) and K2CO3 (7.40 g, 53.5 mmol) were dissolved in dry DMF (30 mL) in a 100 mL two-necked flask. Ethyl butyrate (5.82 mL, 40.7 mmol) was stirred at room temperature overnight. The reaction was completely detected by TLC. The reaction was quenched by the addition of 150 mL of water, extracted with EA (25mL×4), and the organic phase was combined, concentrated, and purified by silica gel column chromatography (gradient elution polarity: PE/EA=50/1-5/1 ) 4.14g of a colorless transparent liquid, yield 45.6percent,

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Lin Xinglong; Xie Hongming; Hu Yangxiao; Li Shiguang; Zhang Yingjun; Tan Yumei; Yuan Mingyun; (124 pag.)CN108948019; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 121507-34-4, The chemical industry reduces the impact on the environment during synthesis 121507-34-4, name is 5-Isopropoxy-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life.

(Step 2) Production of 5-isopropoxy-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-3-amine With cooling with ice, sodium hydride (1.44 g) was added to a DMF (100 mL) solution of the compound (4.84 g) obtained in the step 1, and stirred for 2 hours with cooling with ice. The reaction liquid was cooled to -18 C., and 2-(trimethylsilyl)ethoxymethyl chloride (6.38 mL) was dropwise added thereto. After stirred at -18 C. for 2 hours, this was heated up to room temperature, and further stirred for 1 hour. Aqueous saturated ammonium chloride solution was added to the reaction liquid, then extracted with ethyl acetate, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 40%, gradient, and then methanol/chloroform=from 0% to 20%, gradient) to give the entitled compound (2.28 g, 25%).

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-Isopropoxy-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jitsuoka, Makoto; Nagase, Tsuyoshi; Sato, Nagaaki; Tsukahara, Daisuke; US2011/9622; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 18048-64-1, These common heterocyclic compound, 18048-64-1, name is 1-(3,4-Dimethylphenyl)-3-methyl-1H-pyrazol-5(4H)-one, 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.

Example 8; 3- {N’-[ 1 -(3,4-Dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]- hydrazino)-biphenyl-2,3′-dicarboxylic acid (Compound 108) was prepared as described in Scheme II. ¹H NMR (500 MHz, Acetone-d6) 8 8.10-8.06 (m, 2H), 7.77-7.68 (m, 4H), 7.60 (t, J= 7.6 Hz, 1H), 7.30 (dd, J= 7.8, 1.0 Hz, 1H), 7.19 (d, J= 8.3 Hz, 1H), 2.36 (s, 3H), 2.30 (s, 3H), 2.26 (s, 3H).

The synthetic route of 18048-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIGAND PHARMACEUTICALS INC.; WO2005/118551; (2005); A2;,
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 6825-71-4 as follows. HPLC of Formula: C6H10N4O2

To a solution of ethyl 3,5-diamino-1 -hydro-pyrazole-4-carboxylate (5.00 g, 29.38 mmol)In N, N-dimethylformamide ((80 mL)1,1,3,3-tetramethoxypropane (14.50 mL, 88.15 mmol)And acetic acid (0.34 mL, 5.88 mmol).After the reaction mixture was stirred at 100 C for 14 hours,Concentrate under reduced pressure. The resulting residue was dispersed in a mixed system of dichloromethane (50 mL) and water (50 mL), the organic phase was separated and the aqueous phase was extracted with dichloromethane (100 mL x 3). The combined organic phases were washed with saturated brine (100 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH3 in methanol (7M) / methylene chloride (v / v) = 1/100) to give the title compound as a pale yellow solid (3.52 g, 58.1%).

According to the analysis of related databases, 6825-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; (88 pag.)CN104650092; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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 solution of ethyl 5-amino-lH-pyrazole-4-carboxylate (13.7 g, 88.0 mmol) in DMF (150 mL) was added ethyl (//)-3 -ethoxy aery late (15.2 g, 106.0 mmol) and the reaction mixture was stirred at 1 l0C for 1 h. The reaction mixture was diluted with water, adjusted pH to 2 with 2 N HC1 aqueous. The mixture was filtrated and the residue was washed with water and ethyl acetate and the filtrate was concentrated under reduced pressure to give the title compound as a white solid (18.3 g, 100 %), which used in next step without further purification. ‘H NMR (400 MHz, CDCb): d, 1.28 (t, J= 6.8Hz, 3H), 4.27 (q, J= 12 Hz, 2H), 6.15 (d, J= 7.6 Hz, 1H), 8.13 (s, 1H), 8.57 (d, J= 8.0 Hz, 1H), 11.74 (brs, 1H). ESI-MS (EI+, m/z): 208.1.

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; HATCHER, John M.; POWELL, Chelsea E.; JANNE, Pasi A.; (439 pag.)WO2020/69106; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics