Day: July 27, 2021

These common heterocyclic compound, 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, 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. COA of Formula: C4H3F3N2

To a vial was added 3-iodo-N- isopropyl-l-[(4-methoxyphenyl)methyl]pyrazolo[4,3-c]pyridin-4-amine (100 mg, 0.237 mmol), 4-(trifiuoromethyl)-lH-pyrazole (30.6 mg, 0.225 mmol), copper(I) iodide (11.3 mg, 0.059 mmol), potassium carbonate (57.8 mg, 0.414 mmol). The vial was purged with nitrogen and toluene (0.47 mL, 4.45 mmol) and iras-N,N’-dimethylcyclohexane-l,2- diamine, (0.02 mL, 0.12 mmol) were added. The vial was sealed and heated to 110 C for 24 h. The reaction mixture was filtered through Celite, eluting with DCM and concentrated in vacuo. The crude residue was purified by column chromatography (0-20% EtOAc in DCM) to give the title compound which was used directly in the next step.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHAN, Bryan; ESTRADA, Anthony; SHORE, Daniel; SWEENEY, Zachary; WO2013/139882; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 138907-68-3, name is Ethyl 5-amino-1-(4-fluorophenyl)-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 138907-68-3, Product Details of 138907-68-3

(ii) Ethyl 5-amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxylate (6.83 g, 27.40 mmol) was dissolved in chloroform (180 ml) and bromine (3.23 ml, 63.03 mmol) was added to give a dark red/brown solution. To this isoamyl nitrite (5.52 ml, 41.10 mmol) was added dropwise and the mixture was then stirred at room temperature for 1.5 hrs. The solvent was evaporated to give ethyl 5-bromo-1-(4-fluorophenyl)-1 H-pyrazole-4- carboxylate (15.56 g) as an orange/brown oil which solidified on standing. This was used in the subsequent step without further purification.

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 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/138876; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 34091-51-5, name is 5-Iodo-1-methyl-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 34091-51-5, Computed Properties of C4H5IN2

lsopropylmagnesium chloride (0.55 ml, 1.10 mmol) was added to a solution of 5- iodo-1 -methyl-1 H-pyrazole (208 mg, 1.00 mmol)[ prepared according to Effenberger, F.; Krebs, A. J. Org. Chem. 1984, 49, 4687] in tetrahydrofuran (5 ml) at -78 0C. The reaction mixture was stirred at this temperature for 30 min. A solution of bis(1 ,1-dimethylethyl) (E)- 1 ,2-diazenedicarboxylate (253 mg, 1.100 mmol) in 5 mL of THF was added at -78 0C. The reaction mixture was warmed to RT and saturated NH4CI solution was added to quench the reaction. The organic layer was separated and the aqueous layer was extracted with ether. The combined organic layers were washed with brine, dried (Na2CO3) and concentrated to give the crude product, which was purified on a silica gel column to give 180 mg (57.6%) of product. LCMS MS (M+H+): 313.2.

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

Reference:
Patent; SMITHKLIKE BEECHAM CORPORATION; WO2009/158371; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-Iodo-1-methyl-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 39806-90-1, Safety of 4-Iodo-1-methyl-1H-pyrazole

EXAMPLE 7; rac-3 -[(/ ?,2J?)-2-Hydroxycyclohexyl] -6- { [4-( 1 -methyLiH-pyrazol-4-yl)-3-oxopiperazin- 1 – yl] methyl } benzo [h] quinazolin-4(JH)-oneSynthesis of l-(l-methyl-7H-pyrazol-4-yl)piperazin-2-one.To a solution of /eri-bulyl 3-oxopiperazine-l-carboxylate (0.164 g, 0,819 mmol) in 3 mL of isopropanol under an atmosphere of nitrogen was added l-methyI-4-iodo-/H-pyrazole (0.204 g, 0.983 mmol), ethylene glycol (0.051 g, 0.82 mmol), copper iodide (0.031 g, 0.16 mmol), and potassium phosphate (0.695 g, 3.28 mmol). The reaction was heated to 100C for 8 h; cooled to rt, and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 10-100% ethyl acetate in hexanes to provide tert- butyl 4-(l-methyl-7H-pyrazol-4-yl)-3-oxopiperazine-l-carboxylate that gave a mass ion (ES+) of 281.1 for [M+H .

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; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; BESHORE, Douglas, C.; DIMARCO, Christina, Ng; GRESHOCK, Thomas, J.; WO2011/84371; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5932-30-9, A common heterocyclic compound, 5932-30-9, name is Ethyl 5-phenyl-1H-pyrazole-3-carboxylate, molecular formula is C12H12N2O2, 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.

To a solution of compound 23 (l.08g, 5.00 mmol) and compound 25 (981 mg, 6.00 mmol) in 50 ml acetonitrile was added K2CO3 (1.24 g, 9.00 mmol) and heated to reflux for 8 hours. After cooled to rt, filtered off, the filtrate was concentrated and the residue was purified by silica-gel column chromatography to afford compound 24a (950 mg, 55% yield) and compound 24b (150 mg, 8.7% yield).(compound 24a)LCMS m/z=344 [M+H]+ LC/MS informationColumn: Xbridge C18 (3.5pm 4.6x50mm)Flow rate: 1.8 mL/min UV detection wavelength: 254nmMobile phase’- [A] is 0.05% TFA-containing aqueoous solution, and [B] is 0.05% TFA- containing acetonitrile solutionFrom 0 to 1.5 minutes, the percentage of [B] in the mobile phase was gradually increased from 5% to 100%. Thereafter a solution of 100% of [B] was used as the mobile phase.retention time= 1.41 minutes.(compound 24b)LCMS m/z=344 [M+H]+ LC/MS informationColumn: Xbridge C18 (3.5mu?iota 4.6x50mm)Flow rate: 1.8 mL/minUV detection wavelength: 254nmMobile phase: [A] is 0.05% TFA-containing aqueoous solution, and [B] is 0.05% TFA- containing acetonitrile solutionFrom 0 to 1.5 minutes, the percentage of [B] in the mobile phase was gradually increased from 5% to 100%.. Thereafter a solution of 100% of [B] was used as the mobile phase.retention time= 1.50 minutes

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

Reference:
Patent; Shionogi & Co., Ltd.; YUKIMASA, Akira; WO2012/144661; (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. 473528-88-0, name is 4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C5H5BrN2O

Steps 1-2 (0865) To a mixture of 22 6-bromoisoquinolin-3-amine (XII) (4.0 g, 17.93 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (1.03 g, 1.26 mmol), 174 KOAc (4.39 g, 44.83 mmol) and 175 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (5.01 g, 19.72 mmol) in 33 1,4-dioxane (50 mL) was bubbled with 176 N2 for 2 min. The reaction mixture was sealed and heated at 90 C. for 1.5 h. The reaction was cooled to room temperature, filtered and washed with EtOAc. The filtrate was concentrated and the residue taken in dioxane (50 mL). To the suspension was added 177 4-bromo-2-methyl-pyrazole-3-carbaldehyde (LX) (3.39 g, 17.93 mmol) followed by 32 K3PO4 (9.52 g, 44.83 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (1.03 g, 1.26 mmol) and 24 water (15 mL). The mixture was purged with N2 for a min, sealed and heated again at 90 C. for 19 h. The mixture was cooled to room temperature and concentrated to about 20 mL. The concentrate was diluted with EtOAc and filtered through a pad of Celite. The filtrate was diluted with water and the organic layer separated. The organic layer was washed with brine; dried, filtered and concentrated. The residue was triturated in ether and the resulting solid filtered to afford 178 4-(3-amino-6-isoquinolyl)-2-methyl-pyrazole-3-carbaldehyde (LXI) (4.1 g, 16.2 mmol, 90.6% yield) as a brown solid. 1H NMR (499 MHz, DMSO-d6) delta ppm 0.01 (6H, s), 0.86 (9H, s), 0.88-1.00 (2H, m), 1.23-1.35 (2H, m), 1.35-1.46 (1H, m), 1.69-1.79 (2H, m), 1.85-1.95 (2H, m), 2.21 (1H, tt, J=12.21, 3.57 Hz), 3.38 (2H, d, J=6.31 Hz), 3.57 (3H, s) ESIMS found for C14H12N4O m/z 252.95 (M+1).

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; Samumed, LLC; KC, Sunil Kumar; Mittapalli, Gopi Kumar; Hofilena, Brian Joseph; Marakovits, Joseph Timothy; Chiruta, Chandramouli; Mak, Chi Ching; Cao, Jianguo; (324 pag.)US2017/313681; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 2075-46-9, 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. 2075-46-9, name is 4-Nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 4-nitro-1H-pyrazole (1.13 g, 10 mmol) in DMF (20 ml) was added K2CO3 (1.38 g, 10 mmol) and 2-Bromoethanol(1.50 g, 12 mmol). Then the mixture was stirred at 60 C for 12 h. DMF was removed at reduced pressure and add water (100 ml), extractedwith ethyl acetate (3×100 ml), dried with Na2SO4 and evaporated to give compound 2a as a white solid.

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

Reference:
Article; Ding, Huai-Wei; Wang, Shu; Qin, Xiao-Chun; Wang, Jian; Song, Hong-Rui; Zhao, Qing-Chun; Song, Shao-Jiang; Bioorganic and Medicinal Chemistry; vol. 27; 13; (2019); p. 2729 – 2740;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, molecular formula is C4H5IN2, 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. COA of Formula: C4H5IN2

Step 2: I-methyl-IH-pyrazole-4-carbonitrileTo a solution of 4-iodo-I-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml) was added potassium ferrocyanide (24.5 gm, 0.058 moles),palladium (II) acetate (0.592 gm, 0,0026 moles) and sodium carbonate (27.98 gm, 0.264 moles). The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 90-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 C. The reaction mixture was filtered throughpad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60- 70C, cooled the mixture to 20-30C. Hexane (400 ml) was added to the mixture and stirredfor 1 hour at 20-30C. The solid product obtained was filtered off, washed with cold Dl water (100 ml) and dried at 40-50C to yield the product, 1-methyl-IH-pyrazole-4-carbonitrile,.? Drywt 17.94gmYield 0.32 w/w (63%);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39806-90-1, its application will become more common.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2110; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1904-31-0, 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 1904-31-0 as follows.

To a suspension of 6-((6-bromo-1 H-[1 ,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (68 mg, 0.2 mmol) (prepared from quinolin-6-ylmethanamine following the procedures of Compound 1 ) and 1-methyl-1 H-pyrazol-3-amine (20 mg, 0.22 mmol) in dioxane (5ml_) were added Cs2C03 (72 mg, 0.22 mmol) and H20 (0.5 ml_). The mixture was degassed and charged with N2 three times, then Pd2(dba)3 (0.02 mmol, 18 mg) and xantphos (0.04 mmol, 23 mg) were added. The resulting mixture was stirred at 120°C under one atmosphere of N2 overnight, then concentrated. The resulting residue was purified by chromatography to afford the title compound (10 mg). MS (m/z): 358 (M-M f.

According to the analysis of related databases, 1904-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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. Application In Synthesis of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

To lambda/-(5-(chloromethyl)-2,3-dihydro-7/-/-inden-1-yl)propane-2-sulfonamide (0.250 mmol, 72 mg) in DMF (4 ml.) was added ethyl 3-(trifluoromethyl)-7/-/-pyrazole-4-carboxylate (0.250 mmol, 52.1 mg) and Potassium carbonate (0.750 mmol, 104 mg). The resultant solution was heated to 60 0C with stirring. After 1.5 h the reaction mixture was concentrated to remove DMF before partitioning between EtOAc/H2O and the phases mixed and separated. The organic layer was washed with water (x 4) and brine before drying and concentration to a yellow oil. Purification on 10g Si eluting with 1% MeOH/DCM gave the desired compound as an off-white solid (60 mg, 0.131 mmol, 52.2 %). 1H NMR (400 MHz, CDCI3) delta 1.33 (t, 3H) 1.44 (d, 6H) 1.95 (m, 1 H) 2.65 (m, 1 H) 2.85 (m, 1 H) 3.00 (m, 1 H) 3.25 (m, 1 H) 4.15 (d, 1 H) 4.29 (q, 2H) 4.95 (m, 1 H) 5.30 (s, 2H) 7.14 (s, 1 H) 7.18 (d, 1 H) 7.48 (d, 1 H) 7.88 (s, 1 H).

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

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