Tag: M.W:100-200

These common heterocyclic compound, 41680-34-6, name is 3-Amino-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. Recommanded Product: 41680-34-6

To a stirred solution of 5-amino-1H-pyrazole-4-carboxylic acid (10.0 g, 71.4 mmol) in ethanol (100 mL), was added sodium ethoxide (17.0 g, 245 mmol) followed by 1,3-dimethyluracil (11.0 g, 78.6 mmol). The reaction mixture was then stirred at reflux overnight under an argon atmosphere. The mixture was poured into ice-water, and the resultant solution was acidified to about pH 3-4 with concentrated HCl. The suspension was stirred for 2 hours and then filtered to afford the intermediate, which was used without further purification (10.0 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): 8.54 (d, J=9.2 Hz, 1H), 8.06 (s, 1H), 6.11 (d, J=7.2 Hz, 1H).

The synthetic route of 3-Amino-1H-pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; US2012/22043; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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 4149-06-8, Recommanded Product: 4149-06-8

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1310350-99-2, name is 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-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. Safety of 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid

4-Chloro-l -(difluoromethyl)- 1 H-pyrazole-3 -carboxylic acid (0.083 g, 0.423 mmol) was added to DMTMM (0.117 g, 0.423 mmol) in MeOH (2 mL). After stirring the mixture for 5 minutes, a solution of intermediate 1-12 (0.1 g, 0.384 mmol) in MeOH (2 mL) was added at 0 C, and the mixture was stirred for 24 hours. The solvent was evaporated in vacuo. The residue was then suspended in DCM and treated with sat. aq. Na2C03 sol. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 7 M ammonia in MeOH/DCM 0/100 to 5/95). The desired fractions were collected and concentrated in vacuo. The product was purified further by preparative HPLC (RP, C18 XBridge 30×100 5 urn), mobile phase (gradient 90% 0.1% to 0% 0.1% NH4HCO3/NH4OH pH 9 solution in water, 10% MeCN). The desired fractions were collected and the product was extracted with DCM. The organic layer was separated, dried (MgS04), filtered and concentrated in vacuo. The residue was dried overnight (vacuum oven, 50C) yielding compound 5 (53 mg, 31% yield) as a pale yellow solid.

The synthetic route of 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; WO2014/198854; (2014); 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., name: 3-Methyl-4-nitro-1H-pyrazole

Procedure B:General Procedure for the Synthesis of 4-Amino-3 -methyl- 1-N-alkylated pyrazolesA solution of 3-methylpyrazole (1.96mL, 24.0mmol) in sulfuric acid (15mL) was cooled to – 5C and potassium nitrate (l . leq) was added portion-wise. The reaction was warmed to rt and stirred for 16h. The mixture was cooled to 0C and neutralized with ammonium hydroxide solution. The resulting solid was filtered and air-dried to give 3-methyl-4-nitro- 1H-pyrazole. To a solution of 3-methyl-4-nitropyrazole (300mg, 2.6mmol), potassium carbonate (2eq) and the alkylating reagent (l. leq) in acetonitrile (lOmL) was heated at 60C for 18h. After cooling to rt the mixture was diluted with EtOAc and washed with water. The organic phase was collected, dried (MgSC^) and concentrated in vacuo. The crude residue was dissolved in methanol (lOmL), palladium on carbon (50mg) was added and the reaction was stirred under a balloon of hydrogen for 18h. The resulting mixture was filtered through Celite and the filtrate concentrated in vacuo to give the desired product.Example 23: 2-((6-(l-(2-methoxyethyl)-3 -methyl- 1 H-pyrazo 1-4-ylamino)- 1 H-pyrazo lo [3,4- d]pyrimidin- 1 -yl)methyl)benzonitrileThe following compound was made according to the procedure in Example 1, using l-(2- methoxyethyl)-3 -methyl- lH-pyrazo 1-4-amine. 1 -(2 -methoxyethyl)-3 -methyl- lH-pyrazo 1-4- amine was prepared by Procedure B using l-bromo-2-methoxyethane as alkylating agent:1H NMR (d6-DMSO) delta 9.29-9.36 (m, 1Eta), 8.94 (s, 1Eta), 8.09 (s, 1Eta), 7.89 (d, 1Eta), 7.65 (td, 1Eta), 7.51 (t, 1Eta), 7.28-7.30 (m, 1Eta), 5.68 (s, 2Eta), 4.15 (t, 2Eta), 3.63 (t, 2Eta), 3.18 (s, 3Eta), 2.14 (s, 3H); LC-MS method B, (ES+) 389.1, RT = 7.86min

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; CELLZOME LIMITED; RAMSDEN, Nigel; HARRISON, Richard John; OXENFORD, Sally; BELL, Kathryn; PITON, Nelly; DAGOSTIN, Claudio; BOUSSARD, Cyrille; RATCLIFFE, Andrew; WO2011/48082; (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. 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid

Compounds 41-70 were part of a parallel set prepared in library plate format according to General Procedure L, outlined below. ; L. General Procedure for Plate Preparation-Amide Formation XXI: Resin bound deprotected biarylphenol XVII (prepared from intermediate XII, boronates XIVd and XIVe, following general procedures D-F) was distributed into a 96 well plate, 10 mg of resin (0.013 mmol) per well. To the resin 400 mul of dichloromethane was added, followed by 100 mul of DIEA, followed by 0.13 mmol (10 equiv) of heterocyclic carboxylic acid XXa-XXn was added followed by 61 mg (0.13 mmol, 10 equiv) of PyBrop. The plate was shaken at room temperature for 24 hours, then drained and washed with dichloromethane, methanol/dichloromethane, dimethylformamide, methanol/dichloromethane and dichloromethane. The compounds were cleaved with TFA/dichloromethane (600 mul, 1:1) into a 96 deep well plate and submitted for testing without further purification. (Mass spec results obtained are shown in Table 4). Carboxylic Acids Het-COOH XX:

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; Adolor Corporation; US2006/74086; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 85290-80-8, name is Ethyl 1-methyl-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 85290-80-8, Application In Synthesis of Ethyl 1-methyl-1H-pyrazole-4-carboxylate

Step 2 Preparation of 1-methyl-1H-pyrazole-4-carboxylic acid A solution of 1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (300 mg, 1.95 mmol) in ethanol cooled to 0 C. was treated with a 1N aqueous sodium hydroxide solution. The reaction was then warmed to 25 C. and was stirred at 25 C. for 18 h. At this time, the reaction was concentrated in vacuo and acidified to pH=2 with a 1N aqueous hydrochloric acid solution. This solution was extracted with ethyl acetate (3*50 mL). The organics were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and dried in vacuo to afford 1-methyl-1H-pyrazole-4-carboxylic acid (193 mg, 78.5%) as a white solid: LR-MS for C5H6N2O2 (M-H)+ at m/z=125.

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 1-methyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dunten, Peter W.; Foley, Louise H.; Huby, Nicholas J.S.; Pietranico-Cole, Sherrie L.; Yun, Weiya; US2004/14766; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 3112-31-0, These common heterocyclic compound, 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic 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.

Step 1 To a solution of Compound 1 (60 g, 345 mmol) in methanol (600 mL), under nitrogen atmosphere, thionyl chloride (75 mL, 1034 mmol) was added at 0C, followed by heating at reflux for 4 hours. The reaction solution was concentrated in vacuo to yield crude product 2 (64.3 g). LC/MS (Method A): 0.93 min, [M+H]+ = 185.

Statistics shows that 1H-Pyrazole-3,5-dicarboxylic acid is playing an increasingly important role. we look forward to future research findings about 3112-31-0.

Reference:
Patent; Shionogi&Co., Ltd.; EP2327704; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 110860-60-1, 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. 110860-60-1, name is Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(11) Synthesis of azo pigment (2a) 9.2 g of the intermediate (b) is dissolved in a mixed solution of 55 mL of acetic acid and 37 mL of propionic acid at room temperature. The mixture is cooled with ice to an internal temperature of -3C, and a 40% by weight solution of nitrosylsulfuric acid in sulfuric acid is dropwise added thereto at an internal temperature of from -3C to 4C in 10 minutes. After stirring for 1 hour at an internal temperature of 4C, 0.2 g of urea is added thereto, followed by cooling to an internal temperature of -3C and further stirring for 10 minutes to obtain a diazonium salt solution. Separately, 10 g of the intermediate (d’) is completely dissolved in 150 mL of acetone, and cooled to an internal temperature of 17C, and then added to the above-described diazonium salt solution in 25 minutes at an internal temperature in the range of from-3C to 3C. After completion of the addition, the reaction solution is stirred for 30 minutes at 3C, and the ice bath is removed to allow the internal temperature to rise to room temperature. After stirring the reaction solution at room temperature for 30 minutes, precipitated crystals are collected by filtration, spray washed with 150 mL of acetone, then further spray washed with 100 mL of water. Crystals thus-obtained are suspended in 400 mL of water without drying, and an 8N potassium hydroxide aqueous solution is added thereto to adjust the pH to 5.7. After stirring at room temperature for 20 minutes, resulting crystals are collected by filtration, sufficiently spray washed with water, and then spray washed with 80 mL of acetone. The thus-obtained crystals are dried at room temperature for 12 hours. The thus-obtained crystals are suspended in 580 mL of acetone, and then the mixture is stirred for 30 minutes under reflux. Thereafter, the mixture is cooled to room temperature in 10 minutes, and formed crystals are collected by filtration, and dried at room temperature for 5 hours to obtain 17.1 g of the azo pigment (2a). Yield: 88.5%. Visual observation of the thus-obtained azo pigment (2a) under a transmission microscope (manufactured by JEOL Ltd.; JEM-1010 electron microscope) reveals that the length of the long axis of primary particles is about 15 mum. When X-ray diffraction of the azo pigment (2a) is measured under the aforesaid conditions, characteristic X-ray peaks are shown at Bragg angles (2theta+/-0.2) of 7.6 and 25.6. The X-ray diffraction pattern with characteristic Cu Kalpha line is shown in Fig. 1.

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, Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FUJIFILM Corporation; EP2474575; (2012); 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 5334-40-7 as follows. name: 4-Nitro-1H-pyrazole-3-carboxylic acid

Synthesis of 123-A. To a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (8.00 g, 50.1 mmol) in MeOH (160 mL) was added SOCl2 (11.92 g, 100.2 mmol) dropwise under ice bath. Then the solution was stirred at room temperature overnight. The solution was concentrated in vacuo to give 123-A (8.70 g, 84percent) as a white solid.

According to the analysis of related databases, 5334-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 10199-68-5, 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 10199-68-5 as follows.

(5)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(4-phenyl- lH-pyrazol-l- vDpropanamide (C2iHi7F3 (0721) (0722) [00328] To a solution of 4-phenyl-pyrazole (0.50 g, 0.003468 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil (0.35 g, 0.00867 mol). After addition, the resulting mixture was stirred for 3 h. (7?)- 3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8, 1.22 g, 0.003468 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using ethyl acetate and hexanes (1 :2) as eluent to afford 0.90 g of the titled compound as white needles. (0723) [00329] Compound 1003 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.40 (s, 1H, NH), 8.46 (d, = 2.0 Hz, 1H, ArH), 8.24 (dd, = 8.4 Hz, J = 2.0 Hz, 1H, ArH), 8.09 (d, = 8.4 Hz, 1H, ArH), 8.05 (s, 1H, Pyrazole-H), 7.82 (s, 1H, Pyrazole-H), 7.52-7.45 (m, 2H, ArH), 7.35-7.31 (m, 2H, ArH), 7.20-7.16 (m, 1H, ArH), 6.33 (s, 1H, OH), 4.50 (d, = 14.0 Hz, 1H, CH), 4.30 (d, = 14.0 Hz, 1H, CH), 1.40 (s, 3H, CH3); Mass (ESI, Positive): 415.1455[M+H]+.

According to the analysis of related databases, 10199-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics