Day: August 3, 2021

Related Products of 141573-95-7, A common heterocyclic compound, 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C8H10F2N2O2, 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.

The aniline compound (la to Id) (leq.) and DFMMP (1 eq.), both dissolved in an inert solvent were added to a suspension of a base (1.5 eq.) in the inert solvent at 0C. The conversion of aniline to anilide was followed by GC analyses.

The synthetic route of 141573-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOLVAY SA; BRAUN, Max, Josef; WO2012/55864; (2012); 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. 1191616-45-1, name is 4-(4-Bromophenyl)-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C10H9BrN2

Into a 500-mL 3-necked round-bottom flask, were placed 4-(4-bromophenyl)- 1-methyl-1H-pyrazole (3.80 g, 16.0 mmol) and tetrahydrofuran (50 mL). This was followed by the addition of n-BuLi (7.00 mL, 74.3 mmol) dropwise with stirring at -80 C within 5 min. To this was added 1-benzyl-5-bromo-N- methoxy-N-methyl-1 H-indazole-3-carboxamide (2.00 g, 5.34 mmol, synthesis see below). The resulting solution was stirred for 150 min at -80 C. The reaction was then quenched by the addition of 50 mL of ice water. The resulting solution was extracted twice with 50 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuo. The residue was applied onto a silica gel column with dichloromethane/methanol (100/1). This resulted in 1.70 g (60%) of 5- bromo-3-[[4-(1-methyl-1 H-pyrazol-4-yl)phenyl]carbonyl]-1-(1-phenylpentyl)- 1 H-indazole as a yellow solid.

The synthetic route of 1191616-45-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LTD.; SCHIEMANN, Kai; (173 pag.)WO2016/41618; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, 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 27006-76-4, COA of Formula: C6H7ClN2O

General procedure: To a solution of acetonitrile (20 mL), compound 3 (0.02 mol), benzyltriethylamine chloride (0.001 mol), KOH (0.024 mol), and appropriate phenols were added and refluxed for 5-48 h. The solvent was removed to give a residue under reduced pressure, which was dissolved with CH2Cl2 and washed using 10% KOH solution. Anhydrous MgSO4 was used to dry the dichloromethane layer. Compounds 4a-4l and 5a-5l were obtained after evaporation of the solvents, which were used to prepare compounds 6a-6l and 7a-7l without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Song, Ming-Xia; Wu, Yi; Deng, Xian-Qing; Letters in drug design and discovery; vol. 13; 8; (2016); p. 800 – 808;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 14521-80-3,Some common heterocyclic compound, 14521-80-3, name is 3-Bromo-1H-pyrazole, molecular formula is C3H3BrN2, 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.

General procedure: Pyrazoles 4 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and NBS or NIS (1.5 mmol) were dissolved in 2 mL of EtOAc solvent. the reaction mixture was stirred at room temperature under air for 12 h. After the reaction, the resulting mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and the solvent was then removed under vacuum. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate, 3:1) to afford the corresponding product.

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-1H-pyrazole, its application will become more common.

Reference:
Article; Fu, Lili; Bao, Xiaodong; Li, Shanshan; Wang, Lingtian; Liu, Zhiguo; Chen, Wanzhi; Xia, Qinqin; Liang, Guang; Tetrahedron; vol. 73; 17; (2017); p. 2504 – 2511;,
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. 84547-84-2, name is 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 84547-84-2

A mixture of 4-bromo- 1 -methyl- 1 H-pyrazole-5-carboxylic acid (5.0 g, 24.4 mmol) and BH3.THF (36.6 mL of a 1 M solution in THF, 36.6 mmol) in THF (50 mL) was stirred at 50 C for 2 days; at this point LCMS showed the completion of the reaction. The reaction was cooled to RT and cautiously quenched with aq. 1N HC1 and stirred at RT for 1 h, after which the mixture was extracted with EtOAc (3 X 50 mL). The combined organic extracts were concentrated in vacuo. The residue was chromato graphed (80 g Si02; continuous gradient from 0% to 100% EtOAc in hexanes, 25 min) to give the title compound (3.60 g, 18.9 mmol, 77 % yield) as a white solid. LCMS, [M+H]+ = 193.0.

The synthetic route of 84547-84-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, 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. HPLC of Formula: C8H14N4O

General procedure: We intended to synthesize compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold by using microwave assisted protocol (Scheme 1). In this direction we started the studies for optimization of synthesis of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The optimization studies were initiated by screening of different oxidizing agents as depicted in Table1, see Supplementary data using DMSO:Water in 1:1 proportion to see the conversion in desired product. Amongst all oxidants, the best result was observed with K2S2O8, in equivalence studies for catalyst, 3eq. of catalyst has given maximum yields (Table1, see Supplementary data). Therefore, all reactions were conducted using this condition after optimization of catalyst. However, oxone has also given the product 3a with minor yields. After screening of the catalyst we started study of selectivity for solvent that could affect the formation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 3a. The solvent screening was carried out to find out the best conversion, the mixture of DMSO:H2O in 1:1 proportion has given the best results with excellent yields (Table2, see Supplementary data). The microwave protocols were optimized for this reaction as mentioned in Table 3, see Supplementary data; the reactions carried under different microwave Watt powers have given varied results. Wherein, entry 3(b) (Table3, see Supplementary data) was found to be the best condition for maximum conversion. A series of compounds based on 1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one scaffold was synthesized using these optimized conditions, wherein, all kind of substrates with diversity around aryl ring were chosen for conversion and in all cases products obtained in good to excellent yields (Table1).

The synthetic route of 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, G. Lakshma; Guru, Santosh Kumar; Srinivas; Pathania, Anup Singh; Mahajan, Priya; Nargotra, Amit; Bhushan, Shashi; Vishwakarma, Ram A.; Sawant, Sanghapal D.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 201 – 208;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, molecular formula is C5H9N3, 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. Product Details of 3524-32-1

Step 1 An oven dried 100 mL round bottomed flask equipped with a stirring bar was cooled under nitrogen and charged with 1,3-dimethyl-1H pyrazol-5-amine (491.7 mg, 4.42 mmol) and 45 mL of anhydrous THF (0.1M). The THF solution was treated with solid LiHMDS (1.481 g, 8.84 mmol) and stirred at RT for 5 min after which yellow solids formed. C-2 (500 mg, 2.21 mmol) was added in one portion. The flask was equipped with a reflux condenser, and the reaction mixture heated to 80 C. The reaction was monitored by LCMS and was 90% complete after 2 h at 80 C. The reaction mixture was cooled to RT, and the THF removed on a rotary evaporator. The crude residue was partitioned between DCM and water. The DCM layer was washed with brine, dried (MgSO4) filtered and concentrated. The crude residue was absorbed onto Celite and purified by SiO2 chromatography eluting with an EtOAc/heptane gradient (50 to 100% EtOAc) to afford 328 mg (47%) of 6-bromo-N-(1,3dimethyl-1H pyrazol-5-yl)-isoquinolin-3-amine (82).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3524-32-1, its application will become more common.

Reference:
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 2458-26-6, 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. 2458-26-6, name is 3-Phenyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 1-Delta4′-[3-Methyl-4-(3-phenyl-pyrazol-1-ylmethyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid 1-[4′-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.132 g, 0.3 mmol) and 3-phenyl-1H-pyrazole (0.043 g, 0.3 mmol) were combined in DMF. Sodium hydride (60% in mineral oil; 0.014 g, 0.35 mmol) was added, and the reaction was stirred at room temperature for 1.5 hours. Once no starting material was seen by analytical LCMS, the mixture was diluted with EtOAc and 1N aqueous HCl. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with H2O and brine, and then dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative HPLC to give the title compound.

The chemical industry reduces the impact on the environment during synthesis 3-Phenyl-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; US2011/82164; (2011); 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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C12H12N2O2

Example 33 2-Ethyl-5-phenyl-2H-pyrazole-3-carboxylic Acid Ethyl Ester To a 0 C. mixture of the above-prepared 5-phenyl-2H-pyrazole-3-carboxylic acid ethyl ester (350 mg, 1.62 mmoles) and iodoethane (260 muL, 3.23 mmoles) in DMF (3 mL) was added neat LiH (spatula tip, excess) under a nitrogen atmosphere. The resulting mixture was warmed up to room temperature and stirred overnight. The crude reaction was cooled to 0 C., quenched with aqueous NH4Cl, diluted with ethyl acetate and enough water to dissolve all solids. The phases were separated, and the organic phase was washed sequentially with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The regioisomeric products separated and purified by flash chromatography (silica gel, hexanes/ethyl acetate gradient) to give the title compound (167 mg, 42% yield, higher Rf in hexanes/ethyl acetate) and the undesired regioisomer (175 mg, 44% yield) as white solids. 1H NMR (CDCl3, 400 MHz): 7.81 (d, 2H); 7.40 (dd, 2H); 7.29 (dd, 1H); 7.13 (s, 1H); 4.63 (q, 2H); 4.37 (q, 2H); 1.47 (t, 3H); 1.41 (t, 3H).

The synthetic route of 13599-12-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US6608087; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31108-57-3, The chemical industry reduces the impact on the environment during synthesis 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of crude reactant (122.6 mg, 0.287 mmol, theoretical amount) in anhydrous THF (3 mL) was added 4-cyanopyrazole (134 mg, 1.435 mmol) followed by potassium carbonate (198 mg, 1.435 mmol). The solution was heated at 60 C overnight. Then the solution was diluted with ethyl acetate (200 mL). The resulting solution was washed with brine (2×100 mL), dried overmagnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford desired product SB-5 (12.4 mg, 0.0282 mmol, two steps overall yield=9.8%) and by-product (4.2 mg, 0.00955 mmol, two steps overall yield=3.3%) as white solid. Compound SB-5 1HNMR (400 MHz, CDC13) 5(ppm): 7.86 (s, IH), 7.81 (s, IH), 5.02 (AB, IH), 4.90 (AB, IH), 3.42 (AB, IH), 3.40 (S, 3H), 3.39 (AB, IH), 2.64 (s, IH), 2.61 (t, IH), 1.00-2.25 (m, 23H), 0.67 (s, 3H). LC-MS: rt = 2.32 mm, m/z =440.2 [M+H]+

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, 1H-Pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics