Category: pyrazoles-derivatives

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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., Product Details of 1453-58-3

REFERENCE EXAMPLE 93; Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate; Step b) Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate: A suspension of hexane washed 60percent sodium hydride (3.85 g) in dry dimethylformamide (150 ml) was treated with the dropwise addition of a solution of 3-methylpyrazole (7.75 ml) in dimethylformamide (50 ml) under nitrogen at room temperature. Stirring was continueduntil the gas evolution subsided (10 minutes). A solution of methyl 4-fluoro-2-trifluoromethylbenzoate (17.8 g) fromstep a) in dimethylformamide (50 ml) was added dropwise to the clear solution. After stirring for 30 min. at room temperature the reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic extracts (3x) were dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (Merck 60) with a dichloromethane-hexane gradient (50percent – 75percent) to give 13.6 g of the title product as a colorless solid. m.p. 59-61°C MS (EI, m/z): 284 (M)+.

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; Wyeth; EP1000062; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 7119-95-1, 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. 7119-95-1, name is 1-Nitropyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-Nitropyrazole (1 g) was slowly added to a round-bottomed flask containing H2SO4 (98percent, 5 mL) and stirred for 20 h at room temperature. The reaction mixture was slowly transferred to a beaker containing ice with stirring. The solution was extracted with ether. The organic layer was dried with Na2SO4 then evaporated to afford 4-nitropyrazole as a colorless solid (0.97 g, 96percent). The solid was recrystallized from ether/hexane to get white crystalline compound. m.p. 163?165 °C; FT-IR (KBr, cm?1) 3186 (N?H), 1526 and 1353 cm?1 (NO2). 1H NMR (DMSO-d6) delta: 8.26 (d, 1, 5-H), 6.76 (d, 1, 3-H). EI-MS: m/z 113 (M+·). Anal. Calcd for C3H3N3O2: C, 27.54; H, 3.88; N, 32.42. Found: C, 28.31; H, 3.21; N, 31.38.

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

Reference:
Article; Nageswara Rao; Ravi; Tewari, Surya P.; Venugopal Rao; Journal of Molecular Structure; vol. 1043; (2013); p. 121 – 131;,
Pyrazole – Wikipedia,
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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. 146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Bromo-1-methyl-1H-pyrazol-3-amine

Example 0690 0690-1 A mixture of 4-bromo-1-methyl-1H-pyrazole-3-amine (150 mg), pyridine (2 mL), acetic anhydride (241 muL), and N,N-dimethylpyridine-4-amine (11 mg) was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure, and methanol (3 mL) and a 20% sodium hydroxide aqueous solution (1 mL) were added to the obtained residue, followed by stirring at room temperature for 3 hours. After water and ethyl acetate were added to the reaction mixture, the organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining N-(4-bromo-1-methyl-1H-pyrazol-3-yl)acetamide (79 mg). MS m/z (M+H): 218.

The synthetic route of 146941-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1190380-49-4, name is 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, 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 1190380-49-4, category: pyrazoles-derivatives

Into a 100-mL round-bottom flask was placed compound 14.2 (85 mg, 0.24 mmol, 1.00 eq.), n-BuOH (15 mL), 1-(oxan-4-yl)-1H-pyrazol-4-amine (61 mg, 0.36 mmol, 1.50 eq.), and hydrogen chloride in dioxane (1 mL, 4N). The resulting solution was stirred for 30 h at 110 C in an oil bath and then concentrated in vacuo. The resulting solution was diluted with H20. The pH value of the solution was adjusted to 10 with sodium carbonate and the solids were collected by filtration. The solid was dried under infrared light. This resulted in 71.4 mg (61%) of I-22 as an off-white solid. LC-MS (ESI, m/z): [M+H+]= 481.2; 1H NMR: (4d-MeOD, ppm): 7.881 (1H, s), 7.594 (1H, s), 7.055-7.065QH, m), 6.053-6.063 (1H, m), 4.310-4.411(1H, m), 4.048-4.310 (3H, m), 3.974 (3H, s), 3.623-3.743 (4H, m), 3.537-3.623 (2H, m), 2.634-2.644 (4H, m), 2.275-2.409 (3H, m), 2.019-2.167 (6H, m), 1.335-1.563 (4H, m).

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, 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; BOYCE, Sarah; (135 pag.)WO2017/4133; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 51516-70-2,Some common heterocyclic compound, 51516-70-2, name is 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C10H7FN4, 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: A mixture of theintermediate compounds 2 (1 mmol) and 3 (1 mmol) in ethanol(10 mL) was stirred at reflux for 2 h. After cooling to roomtemperature, the precipitated solid was filtered, and thenrecrystallized from ethanol to give the title compounds 5a-5p.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, its application will become more common.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
Pyrazole – Wikipedia,
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These common heterocyclic compound, 17827-61-1, name is Methyl 1-Methylpyrazole-3-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. COA of Formula: C6H8N2O2

Step B: 1 -Methyl- lH-pyrazole-3-carboxamide (3)A solution of methyl l-methyl-lH-pyrazole-3-carboxylate (1.1 g, 7.9 mmol) in NuEta32Omicron (10 mL) was stirred for 2 h at room temperature. The solvent was evaporated to give the crude product which was used for the next step without further purification.

The synthetic route of Methyl 1-Methylpyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; MCCOMAS, Casey, C.; REGER, Thoma, S.; QI, Changhe; WO2014/150114; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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 1192-21-8, Recommanded Product: 1-Methyl-1H-pyrazol-5-amine

(3 S)-7-(2-Chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methylpyridin-3-yl)methyl)-3 ,4- dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (118 mg, 0.31 mmol), i-methyl-i H-pyrazol-5 -amine (33.0 mg, 0.34 mmol), cesium carbonate (201 mg, 0.62 mmol) and BrettPhos 3rd generation pre-catalyst (14.01 mg, 0.02 mmol) were suspended in tert-butanol (5 mL) and de-gassed for 10 minutes. The reaction was heated to 80 °C for 18 hours under nitrogen. The mixture was cooled to room temperature, diluted with EtOAc (50 mL), washed with saturated aqueous sodium bicarbonate (10 mL) and the layers separated. The aqueousportion was washed with ethyl acetate (50 mL) and the combined organics were dried (sodium sulfate) and concentrated in vacuo to a brown gum (198 mg). The solid was taken up in DMSO (5 mL) and filtered. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, Sji silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents.Fractions containing the desired compound were evaporated to dryness to afford (3 S)-3 -methyl-7-(5 -methyl-2-(( i-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methylpyridin-3 -yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (74.0 mg,54.1 percent) as a white solid. ?H NMR (400 MHz, DMSO, 30 °C) 1.14 (3H, d), 2.32 (3H, s),3.68 (3H, s), 3.81 (1H, d), 4.16 – 4.27 (2H, m), 4.34 (1H, dd), 5.12 (1H, d), 6.26 (1H, d),7.20 (1H, dd), 7.27 (1H, d), 7.33 (1H, d), 7.58 – 7.7 (2H, m), 8.23 (1H, s), 8.35 (1H, d),9.06 (1H, s). mlz: ES+ [M+H]+ 442.

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; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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 1192-21-8, COA of Formula: C4H7N3

Under nitrogen a solution of methyl 4-bromo-l-(3-methoxyphenyl)-lH-pyrazole-3- carboxylate (600 mg, 1.928 mmol, 1.00 equiv), l-methyl-lH-pyrazol-5-amine (563 mg, 5.797 mmol, 1.00 equiv), t-BuXPhos (82 mg, 0.193 mmol, 0.10 equiv), 3rd Generation t-BuXPhos precatalyst (154 mg, 0.194 mmol, 0.10 equiv), t-BuONa (279 mg, 2.903 mmol, 1.50 equiv) in 1 ,4-dioxane (12 mL) was irradiated with microwave radiation for 90 min at 90 °C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (1 : 1) to give the title compound (425 mg, 70percent) as a yellow solid. LC-MS (ES, m/z): 314 [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, 1-Methyl-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, 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 35344-95-7, COA of Formula: C4H4N2O

1-isopropyl-1H-pyrazole-4-carbaldehyde To a solution of lH-pyrazole-4-carbaldehyde (2.0 g, 21 mmol) and 2-iodopropane (5.32 g, 31.5 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.83 g, 20.7 mmol) in one portion. The resulting mixture was stirred at room temperature for 2 hours, before being quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 0-50% EtO Ac/heptane to obtain 1- isopropylpyrazole-4-carbaldehyde (1.2 g, 42% yield). 1H NMR (400 MHz, CDC13) delta 9.86 (s, 1H), 7.97 (s, 2H), 4.54 (p, / = 6.7 Hz, 1H), 1.55 (d, / = 6.7 Hz, 6H).

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; GEHLING, Victor S.; HARMANGE, Jean-Christophe; LAI, Tommy; LIANG, Jun; DRAGOVICH, Peter; ORTWINE, Dan; LABADIE, Sharada; ZHANG, Birong; KIEFER, Jim; WO2015/135094; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 20154-03-4,Some common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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 3-trifluoromethylpyrazole (5.0 g, 36 mmol), triethylamine (7.0 mL, 50 mmol) in dichloromethane (40 mL) was added dimethylsulfamoyl chloride (5.5 mL, 51 mmol), and the reaction mixture was heated at reflux for 2 days. The resulting mixture was cooled to ambient temperature and filtered through a pad of silica gel using dichloromethane as eluent. The filtrate was then concentrated under reduced pressure to give an amber residue. The resulting residue was dissolved in diethyl ether. The ether solution was washed with water, dried (MgSC^), and concentrated under reduced pressure to give 8.71 g of the title compound. 1HNMR (CDCl3) delta 3.01 (s, 6H), 6.65 (s, IH)5 8.03 (s, IH).

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

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/13622; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics