Tag: M.W:100-200

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

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

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

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 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

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 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

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. 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Computed Properties of C7H7N3O

A solution of 3-amino-5-(2-furyl)pyrazole (162 mg, 1.09 mmol) and DIPEA (0.19 mL, 1.09 mmol) in THF (5 mL) was added dropwise to a solution of cyanuric chloride (200 mg, 1.09 mmol) in THF (16.0 mL) at 0 0C. The reaction mixture was stirred at 0 C to room temperature for 2 hours. Then, 1-metyl piperazine (0.12 mL, 1.09 mmol) and DlPEA (0.19 mL, 1.30 mmol) were added to the mixture. The mixture was allowed to stir at room temperature for 3 hours. The solids were filtered off to give compound 11 as white solid (1 10 mg, 14 %). %). 1H NMR (400 MHz, DMSOd6) delta 12.92 (s, IH, NH), 10.38 (s, IH, NH), 7.76 (s, IH, Ar-H), 6.816.61 (m, 3H, Ar-H), 3.77-3.72 (m, 4H, 2CH2), 2.38-2.35 (m, 4H, 2CH2), 2.21 (2, 3H, CH3); ESI-MS: calculated for (C15Hi7ClN8O) 360, found 361 [M+H]+.

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; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; HO, David; DESAI, Neil, P.; WO2010/144550; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 131797-35-8, name is 5-Chloro-3-(trifluoromethyl)-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 131797-35-8, Product Details of 131797-35-8

To a solution of 2-chloro-7-(chloromethyl)-N-ethyl-5-oxo-5H-[l,3]thiazolo[3,2-a]pyrimidine- 3-carboxamide (2 g, 6.53 mmol) in acetonitrile (10 mL) was added 5-chloro-3-(trifluoromethyl)-lH- pyrazole (872 mg, 5.11 mmol), potassium iodide (542 mg, 3.26 mmol), and potassium carbonate (1.8 g, 13 mmol). The resulting mixture was stirred for 1 h at 80 C and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/petroleum ether (1/1) to afford of 2-chloro-7-[[5-chloro-3-(trifluoromethyl)-lH-pyrazol-l-yl]methyl]-N-ethyl-5-oxo-5H- [l,3]thiazolo[3,2-a]pyrimidine-3-carboxamide (1.1 g, 38%) as a yellow solid. LCMS (ESI): M+H + = 441.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-3-(trifluoromethyl)-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; YU, Jiang; WU, Guosheng; YUEN, Po-Wai; VILLEMURE, Elisia; SCHWARZ, Jacob; LY, Cuong; SELLERS, Benjamin; VOLGRAF, Matthew; WO2015/52226; (2015); 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. 15802-80-9, name is 3-(tert-Butyl)pyrazole, A new synthetic method of this compound is introduced below., Product Details of 15802-80-9

Sodium hydride (60% suspension in oil, 0.12 g, 3.0 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (10 mL). 3-tert-butylpyrazole (0.20 g, 1.6 mmol) was added in one portion at ambient temperature, and the stirring was continued until the gas evolution subsided. The (5,11-dihydro-pyrido [2,3-b] [1,5] benzodiazepin-6-yl)- [4-fluoro-2-trifluoromethylphenyl]-methanone of Example 4, Step B (0.50 g, 1.3 mmol) was added in one portion to the clear solution. The mixture was placed in an oil bath (preheated at 130C) for 30 minutes and then heated at reflux for 5 hours. After cooling, the mixture was partitioned between water and ethyl acetate. The organic extracts were dried over sodium sulfate and evaporated to dryness. The crude residue was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with 25% ethyl acetate in hexane provided the title product (0.23 g, 36.0%) as a foam which crystallized by trituration with hexane-ether, m.p. 136-140C. NMR (DMSO-d6, 400 MHz): delta 1.26 (s, 9H, C(CH3)3), 4.17 and 5.45 (dd, 2H, CONCH2), 6.47 (m, 1H, pyrazole CH), 6.54 (m, 1H), 6.68 (m, 1H), 6.80 (m, 1H), 7.00 (m, 1H), 7.28 (m, 1H), 7.60 (m, 1H), 7.87 (m, 1H), 8.04 (m, 1H), 8.13 (m, 1H), 8.47 (m, 1H, pyrazole CH), 9.62 (s, 1H, NH) MS (EI, m/z): 491 [M]+ Anal. Calc’d for C27H24F3N5O: C 65.98, H 4.92, N 14.25. Found: C 65.75, H 4.92, N 13.95

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; Wyeth; EP1000059; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics