Tag: M.W:200-300

Electric Literature of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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.

A saturated aq. solution of NaHCO3 (H mL) was added to a solution of 3-terf-butyl-1 -p-tolyl-1 H- pyrazol-5-amine (WO 2000043384) (206 mg, 0.900 mmol) in DCM (20 mL) and the mixture was cooled to O0C and stirred vigorously whilst trichloromethylchloroformate (325 mul_, 2.70 mmol) was added in a single portion. The vigorous stirring was continued at O0C for a further 80 min. The organic layer was separated and dried and was then evaporated in vacuo to provide 3-te/f-butyl-5-isocyanato-1-p-tolyl-1 /-/-pyrazole, Intermediate B1 as orange oil. This material was pumped for 30 min under high vacuum and was then taken up into THF (6.0 ml.) and kept under nitrogen at O0C and used directly in the next step.

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

Reference:
Patent; RESPIVERT LIMITED; ITO, Kazuhiro; STRONG, Peter; RAPEPORT, William, Garth; MURRAY, Peter, John; KING-UNDERWOOD, John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart, Thomas; JOLY, Kevin; CHARRON, Catherine, Elisabeth; WO2010/67130; (2010); 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. 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

According to the procedure of Buchwald et al . (J. Oxg. Chem. 2004, 69, 5578), to a 350 iaL sealed tube flushed vigorously with nitrogen was added ethyl 3- (trifluoromethyl) – lH-pyrazole-4-carboxylate (20.0 g, 96.1 mmol) , 1-iodobenzene (12.9 inL, 115 mmol), potassium carbonate (27.9 g, 202 mmol), copper(I) iodide (0.915 g, 4.80 mmol), and (IS, 2S) -N1,N2- dimethylcyclohexane-l,2-diamine (1.37 g, 9.61 mmol), followed by degassed (argon) toluene (100 mL) . The mixture was stirred for 24 hours at 1100C, cooled to room temperature, and filtered through a short silica pad which was thoroughly rinsed with toluene and AcOEt- The filtrate was concentrated in vacuo to give ethyl l-phenyl-3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (21 g, 77%) as a solid: 1H NMR (400 MHz, CDCl3) delta 1.39 (t, 3H, J = 7.0 Hz), 4.37 (q, 2H, J = 7.0 Hz), 7.42 (m, IH), 7.52 (m, 2H), 7.72 (m, 2H), 8.48 (m, IH).

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; WO2008/11130; (2008); A2;,
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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 141573-95-7

In a 100 mL reaction flask, add ethyl 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate(38 mmol) represented by formula (II), and then add 10% by mass 30mL NaOH aqueous solution, heated to 60 C and stirred until the reaction solution was transparent, and then naturally cooled to room temperature. The reaction solution was adjusted to pH about 2.0 by adding acid, a large amount of solid was precipitated, filtered by suction, and the filter residue was washed with water and dried to obtain the formula 1) -methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid.

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; Zhejiang University of Technology; Liu Xinghai; Cai Pengpeng; Jin Tao; Tan Chengxia; Weng Jianquan; Wu Hongke; (11 pag.)CN110669007; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 155377-19-8, These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)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.

Reference Example 11 Ethyl 3-trifluoromethylpyrazole-4-carboxylate (5 g), potassium carbonate (3.48 g) and ethyl iodide (2.3 ml) in acetonitrile were heated at reflux overnight. After cooling, ethyl acetate and water were added and the organic phase separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried (magnesium sulphate) and evaporated under reduced pressure to give a yellow oil which was purified by crystallisation in hexane to produce 4-ethoxycarbonyl-1-ethyl-3-trifluoromethylpyrazole as white crystals (3.65 g), 1 H NMR (CDCl3) delta1.25(3H,t), 1.45(3H,t), 4.10(2H,q), 4.20(2H,q) 7.90(1H,s) ppm.

The synthetic route of 155377-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Agriculture Limited; US5480857; (1996); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 155377-19-8, name is Ethyl 3-(trifluoromethyl)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 155377-19-8, Recommanded Product: Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

(R)-lambda/-(5-(hydroxymethyl)-2,3-dihydro-1 H-inden-2-yl)propane-2-sulfonamide (2.82 mmol, 760 mg) was dissolved in DCM (20 mL) and Thionyl Chloride (5.64 mmol, 0.409 mL, 671 mg) added and the solution stirred at room temperature. After 45 min the mixture was concentrated then azeotroped with DCM (4 x 10 mL) to give a yellow oil. To this oil was added DMF (10 mL) and potassium carbonate (8.46 mmol, 1170 mg) followed by ethyl 3- (trifluoromethyl)-1 H-pyrazole-4-carboxylate (2.82 mmol, 587 mg) . The mixture was heated to 60 0C with stirring for 1 h. The reaction was concentrated to remove DMF before partitioning between EtOAc/Water. The phases were mixed and separated and the aqueous phase further washed with EtOAc (x 2). Combined organics were dried and concentrated to give a light yellow oil which was purified on silica eluting with 25% EtOAc/heptane. Desired fractions were collected and concentrated to give (R)-ethyl 1-((2- (1-methylethylsulfonamido)-2,3-dihydro-‘//-/-inden-5-yl)methyl)-3-(trifluoromethyl)- 1H- pyrazole-4-carboxylate as a colourless solid (1.1 1 g, 86 %).1H NMR (400 MHz, CDCI3) delta 1.31 (t, 3H) 1.39 (d, 6H) 2.9 (m, 2H) 3.17 (sept, 1 H) 3.30 (m, 2H) 4.30 (m, 4H) 5.28 (s, 2H) 7.13 (m, 2H) 7.25 (d, 1 H) 7.89 (s, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 330792-70-6, name is 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 330792-70-6

To a solution of I-9 (1.50 g, 5.4 mmol) in DMF (20 mL) is added sodium hydride (60percent dispersion in mineral oil, 0.26 g, 6.5 mmol). The mixture is stirred for 5 min then I-1 (2.39 g, 6.5 mmol) is added. The mixture is heated at 70° C. for 18 h then cooled to ambient temperature. The mixture is partitioned between EtOAc and water then organics are collected, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, Hep to 70percent EtOAc in Hep) to afford I-53 (1.2 g, 47percent) m/z 472.2 [M+H].

According to the analysis of related databases, 330792-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BENTZIEN, Joerg Martin; BERRY, Angela Kay; BOSANAC, Todd; BURKE, Michael Jason; DISALVO, Darren Todd; HORAN, Joshua Courtney; LIANG, Shuang; MAO, Can; MAO, Wang; SHEN, Yue; SOLEYMANZADEH, Fariba; ZINDELL, Renee M.; US2014/45813; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 500011-84-7,Some common heterocyclic compound, 500011-84-7, name is 3-Bromo-1-(dimethylsulfamoyl)pyrazole, molecular formula is C5H8BrN3O2S, 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 trifluoroacetic acid (70 mL) was slowly added [3-BROMO-N, N-DIMETHYL-LH-] [PYRAZOLE-1-SULFONAMIDE] (i. e. the bromopyrazole product of Step A) (57.04 g). The reaction mixture was stirred at room temperature for 30 minutes and then concentrated at reduced pressure. The residue was taken up in hexane, insoluble solids were filtered off, and the hexane was evaporated to afford the crude product as an oil. The crude product was further purified by chromatography on silica gel using ethyl [ACETATE/DICHLOROMETHANE] (10: 90) as eluent to afford an oil. The oil was taken up in dichloromethane, neutralized with aqueous sodium bicarbonate solution, extracted with methylene chloride (3x), dried over magnesium sulfate and concentrated to afford the title product as a white solid (25.9 g), m. p. [61-64 C.] [1H] NMR (CDC13) [8] 6.37 (d, 1H), 7.59 (d, 1H), 12.4 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-1-(dimethylsulfamoyl)pyrazole, its application will become more common.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; STEVENSON, Thomas, Martin; WO2003/106427; (2003); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37687-24-4, The chemical industry reduces the impact on the environment during synthesis 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, I believe this compound will play a more active role in future production and life.

Step 1 : Diethvl 1-(2-frtert-butvl (dimethvl) silvl1OxvUethvl)-1H-Pvrazole-3r5- dicarboxylate; To a solution of diethyl 3, 5-pyrazoledicarboxylate (2.17 g, 10 mmol) in acetonitrile (10 ml), under nitrogen, was added potassium carbonate (2.07 g, 15 mmol), and 2- bromoethoxy-t-butyldimethylsilane (2.90 g, 12 mmol). The mixture was stirred at reflux for 18 hr. It was then cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered through Magnesol. The filter pad was eluted wtih 2 x 10 ml of ethyl acetate, and the combined filtrate was evaporated. The residue was dissolved in hexanes and passed through a column of silica gel (70 g). After eluting with hexanes (100 ml), the column was eluted with ethyl acetate. The ethyl acetate eluent was evaporated to give 3.71 g of a colorless oil ; MS m/e 371 (MH+).

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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2003/93279; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

5932-30-9, name is Ethyl 5-phenyl-1H-pyrazole-3-carboxylate, 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 Ethyl 5-phenyl-1H-pyrazole-3-carboxylate

Reference Example 24 Ethyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrazole-3-carboxylate Sodium hydride (60% in oil, 612 mg) was washed with hexane, suspended in N,N-dimethylformamide solution (5 mL), and a solution of ethyl 5-phenyl-1H-pyrazole-3-carboxylate (3.0 g) in N,N-dimethylformamide (10 mL) was added dropwise. After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 min, and added dropwise to an ice-cooled solution of p-toluenesulfonyl chloride (3.16 g) in N,N-dimethylformamide (10 mL). After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=9:1?1:1) to give the title compound as a colorless solid (yield 1.037 g, 20%). 1H-NMR (CDCl3) delta: 1.42 (3H, t, J=7.4 Hz), 2.43 (3H, s), 4.43 (2H, q, J=7.4 Hz), 7.03 (1H, s), 7.30-7.50 (5H, m), 7.75-7.85 (2H, m), 8.07 (2H, d, J=8.4 Hz).

The synthetic route of 5932-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2005957; (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. 153687-35-5, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Safety of 1-(4-Methoxybenzyl)-1H-pyrazole-4-carbaldehyde

1H-PYRAZOLE-4-CARBALDEHYDE (55). To a solution of 1- (4-METHOXY-BENZYL)-1H- pyrazole (0.21 mol) (Synth. Commun. 1990, 20/18 ; 2849) in dry DMF (235 ml) was added POCL3 (1.5 eq. ) dropwise at room temperature. The mixture was then heated at 95°C for 16 hrs. After cooling to room temperature, the reaction mixture was neutralized by adding ice and saturated sodium carbonate solution. EtOAc (800 ml) was added and the organic layer was separated and washed several times with water. After drying (Na2SO4), the solvent was removed and the crude product was purified over silica gel to give 16.4 g (35percent yield) desired aldehyde 1-(4-METHOXY-BENZYL)-LH- pyrazole-4-carbaldehyde. It was heated with 150 ml TFA for 2 hrs. TFA was evaporated and the basified crude product was purified on silica gel to give 5.3 g of 55.

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; IMCLONE SYSTEMS INCORPORATED; WO2005/813; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics