Category: pyrazoles-derivatives

Application 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.

Step 1: Preparation of Methyl 1-(N,N-dimethylsulfamoyl)-1H-pyrazole-4-carboxylate To a solution of methyl 1H-pyrazole-4-carboxylate (0.3 g, 2.4 mmol) and DBU (0.39 mL, 2.6 mmol) in acetonitrile (12 mL) was slowly added dimethylsulfamoyl chloride (0.27 mL, 2.51 mmol). The reaction mixture was stirred at rt for 1 h and was then concentrated under reduced pressure. The resulting residue was partitioned between water and ethyl acetate. The organic phase was washed with 10% citric acid, water, and brine. The organic phase was dried over MgSO4, filtered, concentrated and purified by silica gel chromatography eluting with a gradient of 5% ethyl acetate in DCM, to provide methyl 1-(N,N-dimethylsulfamoyl)-1H-pyrazole-4-carboxylate (0.54 g), LCMS-ESI (POS.) m/z 310.0 (M+H)+.

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; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, 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 1260243-04-6, Computed Properties of C6H9N3O2

Example C.22 5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid; a. A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160 C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0 C. for 0.5 h. The crystals were isolated by filtration and triturated for 1.2 h with 0.2 N HCl (80 mL). The solid was filtered off, washed with water and dried to give ethyl 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (13.3 g, 52%). White solid. MS (ISN) 316.3 [(M-H)-]; mp 190-192 C.

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; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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.

21F. 2-((4-(5-Cyclopropyl-lH-pyrazol-3-ylamino)pyrrolo [1,2-f][l,2,4]triazin-2- yl)methyl)isoindoline-l,3-dione. 2-((4-Chloropyrrolo[l,2-/|[l,2,4]triazin-2-yl)methyl)isoindoline-l,3-dione (4.43 g, 14.17 mmol) was suspended in NMP (50 mL), then DIPEA (4.95 mL, 28.3 mmol) was added. The mixture was heated to 80 0C, to which was slowly added via syringe a solution of S-cyclopropyl-lH-pyrazol-S-amine (3.49 g, 28.3 mmol) in NMP (20 mL). The reaction was stirred at 80 0C for 2 h, then cooled to room temperature. The reaction was diluted with EtOAc (700 mL) and washed with water (3 x 500 mL) and brine (2 x 250 mL). The organics were dried (MgSO4), filtered, and concentrated in vacuo. The residue was dissolved in a minimum of EtOAc and diluted with hexanes, and the precipitate was filtered and dried. The solids were triturated twice with 20% EtOAc/Hex, once with 20% DCM/Hex, and finally in 50% DCM/Hex to give 21F (3.35 g, 59%). 21F had an analytical HPLC retention time = 3.368 min (Phenomonex-Luna (4.6 x 50 mm SlO); 10-90% MeOH/H2O (0.1% TFA) over 4 min; flow = 4 mL/min) and a LC/MS M+ +1 = 400.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Cyclopropyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/131050; (2008); A1;,
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

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, Product Details of 398495-65-3

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 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

Related Products 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

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. 118430-73-2, name is 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., name: 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine

5-Amino-3-tert-butyl-1-methylpyrazole (1.32 g) was added to a stirred solution of phenyl {3- [ (2-chloropyrimidin-5-yl) ethynyl] phenyl} carbamate (Intermediate 35) (2.0 g) in THF (120 mL) and triethylamine (1.2 mL) and the reaction mixture was heated at 65C for 8 hours. The solvent was evaporated and the residue was triturated with ether/DCM to give the title compound as an off-white solid (1.5 g, 64%); MS m/e MHF 409.

The synthetic route of 118430-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/60970; (2005); 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 6825-71-4 as follows. Computed Properties of 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

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. Product Details of 943541-20-6

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