Day: June 24, 2021

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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Methyl-4-nitro-1H-pyrazole

To a solution of cw-3-benzyloxycyclobutanol (17 g, 95 ,4 mmol) and 3-methyl-4-nitro-lH-pyrazole (12.1 g, 95.4 mmol) in THF (350 mL) was added PPh3 (37.5 g, 143 mmol). Then, DIAD (28.9 g, 143 mmol) was added slowly at 0 C, and the mixture was stirred at 15 C for 20 h. The mixture was quenched with H2Q (100 mL), then filtered. The filtrate was then extracted with EtOAc (3 x 70 mL), The organic phase was washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by silica gel colum chromatography (PE:EtOAc = 10: 1 to 7: 1), to give trans- l-(3-benzyloxycyclobutyl)-5-methyl-4-nitro-pyrazole and trans-l-(3- benzyloxycyclobutyl)-3-methyl-4-nitro-pyrazoleTo a solution of /ra>v-l-(3-benzyloxycyclobutyl)-5-methyl-4-nitro-pyrazole and rra?is-l-(3-benzyloxyxyck)butyl)-3-methyl-4-nitro-pyrazole (19.5 g, 67.9 mmol) in DCM (200 mL) was added BC1 (1 M, 26.5 mL) at 0 C, and the mixture was stirred at 0 C for 2 h. The mixture was poured into water (200 mL) slowly, then extracted with DCM (2 x 100 mL). The organic phase was washed with aqueous ai K ()·. (50 mL), brine (40 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (PE/EtOAc = 2 : 1 to 1 : 1), to give trans-3-[5- methyi-4-nitro-pyrazol- 1 -yl]cyclobutanol and rr s-3-[3-metiiyl-4-nitro-pyrazoi-l-yl]cyclobutanol as a mixture as a white soli d .

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); 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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 5932-27-4

(ethyl 1H-pyrazole-3-carboxylate, 1.050 g, 7.49 mmol) was dissolved in ACN (20 mL)Cs2CO3 (2.4 g, 1.0 eq) was added. After stirring for 30 minutes, 4-chlorobenzyl bromide (1.7 g, 1.1 eq) was further added, and the mixture was stirred at room temperature for 5 hours.The solvent was evaporated off, extracted with MC, treated with MgSO4, filtered, and silica-columned with EA: Hex (1: 3) to give starting material 1 (836 mg, 42percent).

According to the analysis of related databases, 5932-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE CATHOLIC UNIVERSITY OF KOREA INDUSTRY-ACADEMIC COOPERATION FOUNDATION; Yu, Ji-Chang; Yu, Kyung-Lee; Koh, Yoon-Jeoung; (20 pag.)KR2016/137199; (2016); A;,
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. 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

Production Example 13-2 tert-Butyl 4-(4-(ethoxycarbonyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate tert-Butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate described in Production Example 13-1 (2.7 g, 9.67 mmol) and commercially available ethyl 4-pyrazole carboxylate (1.49 g, 10.6 mmol) were dissolved in N,N-dimethylformamide (30 mL), 50-72% oily sodium hydride (570 mg) was added at 0 C., and the mixture was heated and stirred at 60 C. for 11 hours. The reaction mixture was cooled to room temperature and water and ethyl acetate were added for partition. The organic layer was washed with water twice and then dried over anhydrous sodium sulfate and filtered. The solvent was evaporated, the resultant residue was dissolved in dichloromethane, the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1-1:3-0:1), and the target fraction was concentrated under vacuum to obtain the title compound (2.11 g, 68%). 1H-NMR Spectrum (CDCl3) delta (ppm): 1.34 (3H, t, J=7.1 Hz), 1.47 (9H, s), 1.82-1.96 (2H, m), 2.10-2.18 (2H, m), 2.82-2.96 (2H, m), 4.19-4.34 (3H, m), 4.29 (2H, q, J=7.1 Hz), 7.91 (1H, s), 7.92 (1H, s).

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; Eisai R&D Management Co., Ltd.; Funasaka, Setsuo; Okada, Toshimi; Tanaka, Keigo; Nagao, Satoshi; Ohashi, Isao; Yamane, Yoshinobu; Nakatani, Yusuke; Karoji, Yuki; US2014/235614; (2014); 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. 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H7ClN4

General procedure: In a round bottomed flask of 100 mL equipped with a condenser we added a solution of 2-substituted-3-aminopyrrole-4-carbonitrile 4 (1 mmol) with either cyclopentanone or cyclohexanone (1.4 mmol) in 30 mL of distilled 1,2-dichloroethane.Anhydrous AlCl3 (4 mmol) was then added, and the mixturewas refluxed for 30 and 32 min, respectively, under microwaveirradiation (at a constant power of 400 W). The mixture wasthen cooled to room temperature. After cooling a mixture oftetrahydrofurane and water (1 : 1, 20 mL) was added, followedby the drop wise addition of NaOH (aq. solution 10%) untilthe solution was basic. After this, the mixture was stirred for30 min, and extracted with dichloromethane (3×20 mL). Thecombined extracts were washed with saline (20 mL), driedover MgSO4, filtered, and the solvent evaporated to obtain asolid, which was identical in all respects with that obtainedfrom the thermal method (mp, TLC, NMR).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 51516-67-7.

Reference:
Article; Alshareef, Hossa Fahad; Mohamed, Heba Abd El Hady; Salaheldin, Abdellatif Mohamed; Chemical and Pharmaceutical Bulletin; vol. 65; 8; (2017); p. 732 – 738;,
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 5932-27-4 as follows. COA of Formula: C6H8N2O2

To an N,N-dimethylformamide solution (2.0 ml) of ethyl 1H-pyrazole-3-carboxylate (111 mg, 0.79 mmol), sodium hydride (60percent in oil, 70 mg, 1.75 mmol) was added under ice-cooling. The resulting mixture was stirred for 5 min. To the reaction mixture, an N,N-dimethylformamide solution (5.0 ml) of compound 26 (815 mg, 1.71 mmol) and tetrabutylammonium iodide (209 mg, 0.56 mmol) were added. While warming to room temperature, the resulting mixture was stirred for 14 h. The reaction mixture was concentrated in vacuo. To the residue, diethyl ether and distilled water were added. The organic layer was separated and dried over Na2SO4. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (methanol-dichloromethane = 1:100) to give the title compounds, 3-isomer (92 mg, 0.18 mmol, 10percent) and 5-isomer (78 mg, 0.15 mmol, 9percent), respectively. 3-isomer: MS (ESI) m/z 522 (M+H)+. 1H NMR (CDCl3) delta 1.38 (3H, t, J = 7.1 Hz), 2.56-2.69 (2H, m), 3.43 (3H, s), 3.86 (3H, s), 4.28-4.34 (1H, m), 4.38 (2H, q, J = 7.1 Hz), 4.43-4.63 (2H, m), 5.74 (1H, s), 6.27-6.32 (1H, m), 6.35-6.38 (1H, m), 6.71-6.77 (2H, m), 6.97 (1H, dd, J = 8.1, 1.5 Hz), 7.07-7.10 (1H, m), 7.21 (1H, t, J = 8.0 Hz), 7.29-7.39 (3H, m), 7.44 (1H, d, J = 2.2 Hz). 5-isomer: MS (ESI) m/z 522 (M+H)+. 1H NMR (CDCl3) delta 1.33 (3H, t, J = 7.1 Hz), 2.48-2.67 (2H, m), 3.43 (3H, s), 3.85 (3H, s), 4.30 (2H, q, J = 7.1 Hz), 4.38-4.46 (1H, m), 4.81-4.90 (2H, m), 5.72 (1H, s), 6.31-6.40 (2H, m), 6.73 (1H, d, J = 2.2 Hz), 6.81 (1H, d, J = 2.0 Hz), 6.95 (1H, dd, J = 8.1, 1.2 Hz), 7.08 (1H, t, J = 2.1 Hz), 7.19 (1H, t, J = 8.1 Hz), 7.28-7.38 (2H, m), 7.40-7.46 (2H, m).

According to the analysis of related databases, 5932-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ichikawa, Masanori; Ohtsuka, Masami; Ohki, Hitoshi; Haginoya, Noriyasu; Itoh, Masao; Sugita, Kazuyuki; Usui, Hiroyuki; Suzuki, Makoto; Terayama, Koji; Kanda, Akira; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 3072 – 3093;,
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. 121507-34-4, name is 5-Isopropoxy-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., SDS of cas: 121507-34-4

2-Chloro-5-fluoro-6-(‘5-isopropoxy-li:/-pyrazol-3-ylamino)nicotinonitrile A solution of 5-isopropoxy-17f-pyrazol-3-amine (0.96g, 6.8 mmol), 2,6-dichloro-5- fluoronicotinonitrile (1.3g, 6.8 mmol), and triethylamine (0.9g, 8.8 mmol) in THF (30 ml) was heated to 60 C for 4 days, and then cooled to 25 C, at which point the product precipitated. The resulting solid was filtered and washed with hexanes (100 ml) to give the title compound (LOg, 50%). MS: Calcd.: 295; Found: [M+H]+ 296.

The synthetic route of 121507-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 4054-67-5, 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. 4054-67-5, name is 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: ,3?,5,5?-Tetramethyl-4,4?-bipyrazole (Me4bpz) was synthesized according to literature methods [33], using acetyl acetone (Acros, 99+ %), sodium hydride (Acros, 60% dispersion in mineral oil), iodine (Sigma-Aldrich, 99.8%) as well as hydrazine hydrate (Merck, ca. 100%). Diethyl ether was dried with sodium/benzophenone and stored under nitrogen atmosphere. All other solvents were used as obtained. Diphenic acid (Acros, 99%) as well as the metal acetate hydrates were used as obtained from the distributors stated above. Metal acetate hydrates, diphenic acid and 3,3?,5,5?-tetramethyl-4,4?-bipyrazole were reacted under hydrothermal conditions (solvent volume: 5 ml) in amounts specified in Table 1 . The autoclaves of type 4749 (Parr, volume 23 ml, Teflon liner, Tmax = 250 C, pmax = 124 bar) were tempered using a drying oven ULE400 (Memmert) with RS232-interface and the control software CELSIUS2000 (Memmert). The reaction vessels were heated to 150 C within 10 h. After 20 h at 150 C the autoclaves were cooled to 25 C within 120 h with constant cooling rate. The generated crystalline solids were filtrated from the liquids and washed with 50 ml hot water and 50 ml hot methanol. Thereafter the products were dried at 120 C in a drying oven. All syntheses were performed at least two times to ensure reproducibility of the results.

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, 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hunger, Jens; Inorganica Chimica Acta; vol. 397; (2013); p. 60 – 68;,
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. 288-13-1, name is 1H-Pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 288-13-1

To a solution of copper(I) oxide (0.906 g, 6.33 mmol), salicylaldoximine (3.47 g, 25.3 mmol), 1H-pyrazole (12.93 g, 190 mmol), and cesium carbonate (66.0 g, 203 mmol) in acetonitrile (50.6 ml) under a nitrogen stream was added 3-bromopyridine (20 g, 127 mmol). The reaction mixture was heated at reflux for 24H. The reaction mixture was allowed to cool to ambient temperature, and then diluted with EtOAc, filtered through celite, and washed with H2O and saturated brine solution. The organics were separated, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 0-50% acetone in hexanes to afford 3-(1H-pyrazol-1-yl)pyridine as a yellow oil (17 g, 93%): 1H NMR (400 MHz, acetone-d6) delta 9.14 (d, J=2.2 Hz, 1H), 8.54 (d, J=3.8 Hz, 1H), 8.45 (dd, J=2.5, 0.5 Hz, 1H), 8.24 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.79 (d, J=1.5 Hz, 1H), 7.53 (ddd, J=8.3, 4.7, 0.7 Hz, 1H), 6.59 (dd, J=2.5, 1.8 Hz, 1H); EIMS m/z 145.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 288-13-1.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37622-90-5,Some common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, molecular formula is C6H8N2O2, 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.

[00615] To the solution of 196-1 (1 g, 7.1 mmol, 1 eq) in EtOH (6 mL) and H20 (10 mL) was added NaOAc (2.2 g, 27.1 mmol, 3.8 eq) and Br2 (5.1 g, 32.1 mmol, 1.7 mL, 4.5 eq). The mixture was stirred at 10 C for 16 hr. The reaction was monitored by TLC. To the reaction mixture was added sodium thiosulfate (2 g), and the solvent was evaporated under reduced pressure. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over Na2S04. The solvent was evaporated under reduced pressure to give 196-2 (1.8 g, crude).

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); 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. 14521-80-3, name is 3-Bromo-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 14521-80-3

Compound 1: 2-(3-(cyclopropylsulfonyl)-1H-pyrazol-1-yl)-N-(5-methoxythiazolo[5,4-b]pyridin-2-yl)-3-(tetrahydro-2H-pyran-4-yl)propanamide 3-bromo-1H-pyrazole (1.0 g, 6.8 mmole), NiBr (0.148 g, 0.68 mmole), 2,2′-bipyridine (0.106 g, 0.68 mmole), Zinc dust (0.993 g, 13.6 mmole) and 1,2-dicyclopropyldisulfane (0.993 g, 6.8 mmole) were added to a solution of DMF (20 mL) and the mixture was heated under N2 for 18 h at 80 C. The solvent was removed from the crude reaction mixture under vacuum and the orange gum was treated with MeOH. The resulting ppt was filtered and discarded. Purification of the filtrate with preparative scale HPLC afforded compound 1A as light brown oil (367 mg). [M+H] calc’d for C6H9N2S, 141.04; found 141.0. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.73 (q, J=5.05 Hz, 2H) 1.02-1.17 (m, 2H) 2.26 (ddd, J=7.58, 3.66, 3.41 Hz, 1H) 6.48 (br. s., 1H) 7.82 (br. s., 1H).3-(cyclopropylthio)-1H-pyrazole (1A) (0.083 g, 0.6 mmole) was dissolved in NMP (2 mL) and the solution was chilled to 0 C. NaH (0.060 g, 1.8 mmole) was added and when the reaction subsided methyl 2-bromo-3-(tetrahydro-2H-pyran-4-yl)propanoate (0.060 g, 1.8 mmole) was introduced, and the reaction was heated at 80 C. for 1 h. The reaction was cooled and quenched with a small volume of MeOH and the crude mixture was purified using preparative scale HPLC. Compound 1B as well as a small amount of the carboxylic acid of 1B were collected. Removal of the solvent and treatment of the acid with TMSCH2N2 followed by combination with 1B afforded title compound as oil (81 mg). [M+H] calc’d for C15H23N2O3S (1B ester), 311.14; found 311.0; [M+H] calc’d for C14H21N2O3S (1B acid), 297.12; found 297.0.Compound 1B used directly from the preceding step was treated with Oxone (0.147 g, 0.24 mmole) in a 1:1 solution of THF/H2O (10 mL). After oxidation was judged complete the solvent was removed and the residue was portioned between EtOAc and H2O. The organic layer was separated, dried and concentrated to yield crude compound 1C as oil. This material was purified using preparative scale HPLC and used directly in the next step, [M+H] calc’d for C15H23N2O5S, 343.12; found 343.3.5-Methoxythiazolo[5,4-b]pyridin-2-amine (0.048 g, 0.26 mmole) was added to a microwave vial followed by DCE (2 mL). The reaction mixture was cooled to 0 C. under a N2 atmosphere. Trimethyl aluminum (2M in hexanes) (0.13 mL, 0.26 mmole) was added and when the reaction subsided the cooling bath was removed, the solution was then stirred at RT for 15 min. To this was added a solution of methyl 2-(3-(cyclopropylsulfonyl)-1H-pyrazol-1-yl)-3-(tetrahydro-2H-pyran-4-yl)propanoate 1C (0.015 g, 0.04 mmole) in DCE (2 mL) and the reaction mixture was heated in a microwave at 110 C. for 1 h. The reaction was then quenched with 1N HCl and extracted 2× with DCM. The organic layers were pooled, dried over Na2SO4; the solvent was removed and the crude residue was purified by preparative scale HPLC to afford compound 1 (46 mg). [M+H] calc’d for C21H26N5O5S2, 492.13; found 492.0. 1H NMR (400 MHz, MeOD) delta ppm 1.07 (dd, J=7.96, 2.15 Hz, 2H) 1.18-1.42 (m, 6H) 1.52 (d, J=9.35 Hz, 1H) 1.74 (d, J=2.02 Hz, 1H) 2.14 (t, J=6.32 Hz, 1H) 2.32 (t, J=10.48 Hz, 1H) 2.61-2.80 (m, 1 H) 3.29 (m, 1H, under MeOD signal) 3.79-3.98 (m, 5H) 5.50 (ddd, J=10.80, 5.68, 5.49 Hz, 1H) 6.81-6.90 (m, 2H) 7.94 (d, J=8.84 Hz, 1H) 8.10 (d, J=2.53 Hz, 1H)

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA SAN DIEGO, INC.; US2009/286800; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics