Category: pyrazoles-derivatives

Application of 14531-55-6, These common heterocyclic compound, 14531-55-6, name is 3,5-Dimethyl-4-nitro-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.

General procedure: A solution of 1.85g (0.01mol) of 2,4,6-trichloro-1,3,5-triazine in the 50mL THF was stirred at room temperature for 1h. Then, 3,5-dimethylpyrazole (2.94g, 0.03mmol) were added into the solution in batches. 5mL of triethylamine was added dropwise whilst stirring at room temperature. After 1h, the mixture was heated at 80C for 1h. After cooling and filtering off, the filtrate evaporated on a steam bath and then washed with hot-water.

Statistics shows that 3,5-Dimethyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 14531-55-6.

Reference:
Article; Wang, Ji-Xiao; Zhu, Zi-Ran; Bai, Feng-Ying; Wang, Xin-Yu; Zhang, Xiao-Xi; Xing, Yong-Heng; Polyhedron; vol. 99; (2015); p. 59 – 70;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, 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. Computed Properties of C5H6N2O2

A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 C. The reaction mixture was stirred for 1 h at 70 C, and then a second portion of potassium permanganate (111 g) was added at 70 C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 C. The reaction mixture was stirred a further 2 h at 70 C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 mL. The aqueous was chilled to 0 C, acidified with concentrated HC1, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57%). Dimethyl sulfate (236 g, 177 ML, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20% aqueous sodium hydroxide (850 ML) at 40 C. The reaction mixture was heated at 80 C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HC1, the precipitate filtered, washed with water, and dried under vacuum to yield 1-METHYLPYRAZOLE-5-CARBOXYLIC acid (85 g, 38%). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid. A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 ML) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension of Pd-C (10 wt%, 9.3 g) in toluene (500 ML), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63%) as a low melting white solid (bp = 92 C @ 8 MMHG).

The synthetic route of 1-Methyl-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58763; (2004); A1;,
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 120068-79-3 as follows. name: 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

General procedure: A mixture of compound A (5 mmol) and corresponding benzaldehyde (5 mmol) in 10 mL ethanol was refluxed for 24 hours in a reaction flask wrapped up by silver paper. Upon the reactions completed (monitored by TLC), tawny solids were obtained through suction filtration. The precipitates were washed with ethanol (5 mLx3) and recrystallized from ethanol with 50-84% yields.

According to the analysis of related databases, 120068-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Letter; Li, Guanglong; Zhou, Cong; Zhu, Chengchun; He, Lujue; Li, Xiaoyang; Xu, Zhiping; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong; Cheng, Jiagao; Letters in drug design and discovery; vol. 16; 10; (2019); p. 1175 – 1180;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, molecular formula is C5H6N2O, 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. category: pyrazoles-derivatives

Step 2: 3-(2-Methyl-2H-pyrazol-3-yl)-acrylonitrile (4): To a stirred solution of 2-methyl-2H-pyrazole-3-carbaldehyde 3 (3.8 g, 0.0345 mol) in toluene (50 mL) was addedcyanomethyl triphenylphosphonium chloride (12.8 g, 0.0389 mol) at room temperature. DBU (1.52 mL, 0.0099 mol) was then added dropwise and heated to reflux for 3 h. After completion of the reaction, the toluene was distilled off completely under vacuum. The resultant crude product was purified on combi flash, with the desired product eluted in 15% EtOAc:Hexane toafford the product (1.1 g, 24.01% yield) as a white solid. ?HNMR(400 MHz, CDC13) oe 7.46-7.45 (d, J 176Hz, 1H), 7.3-7.25 (m, 1H), 6.56 (s, 1H), 5.79-5.75 (d, J= 16.34Hz, 1H), 3.93 (s, 3H). LC-MS (ES, m/z): [M+Hj 134.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27258-33-9, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MILLER, John; BASTOS, Cecilia, M.; MUNOZ, Benito; (155 pag.)WO2017/112853; (2017); 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. 15802-75-2, name is 4-Iodo-3-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 15802-75-2

Compound 34H and Compound 34I: 1-[3-(Benzyloxy)propyl]-4-iodo-3-methyl-1 /-/-pyrazole and 1 -[3-(benzyloxy)propyl]-4-iodo-5-methyl-1 H-pyrazoleA mixture of 3-methyl-4-iodopyrazole (2.59 g, 12.5 mmol) and 1 -bromo-3- benzyloxypropane (3.00 g, 13.1 mmol) in DMF (1 1.4 mL) was charged with potassium carbonate (2.07 g, 15.0 mmol). The reaction mixture was allowed to stir at rt for 16 hrs overnight. The reaction mixture was quenched with water and then extracted with EtOAc. The organic layer was washed with water, brine (2x), dried over sodium sulfate, filtered, and then concentrated in vacuo to yield an oil. The crude material was purified using a Teledyne ISCO Combiflash Rf system [Heptane/EtOAc (100:0? 0:100)] to afford the title products as a mixture of regioisomers (3.60 g, 41 % combined yield). The reaction was carried onto the next step without any further purification. MS (ESI): m/z = 357.02 [M+H]+. UPLC: tR = 1.62 min (UPLC-TOF: polar_3 min).

The synthetic route of 15802-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (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. 398495-65-3, name is 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 398495-65-3

A: starting materials i) 3-[(3,3-Dimethyl-2-oxo-2,3-dihydro-lH-mdole-6-carbonyl)-amino]-4,6- dihydro-pyrrolo[3>4-c]pyrazole-l,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester3,3-Dimethyl-2-oxo-2,3-dihydro-lH-indole-6-carboxylic acid (3.0 g, 14.62 mmol) was dissolved in thionylchloride (19.1 mL, 163 mmol) and after addition of N,N- dimethylformamide (DMF) (200 muL) the mixture was refluxed for 1.5 hours. The volatiles were carefully removed under reduced pressure and the resulting 3,3- dimethyl-2-oxo-2,3-dihydro-lH-indole-6-carbonyl chloride was added portionwise to a mixture of 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-l,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (4.33 g, 14.62 mmol) in dry dichloromethane (DCM) (40 mL) and ethyl-diisopropyl-amine (DIEA) (2.53 mL, 14.62 mmol). The resulting mixture was stirred for 30 minutes, washed with water (20 mL) and brine (20 mL) and evaporated to dryness. Purification by flash chromatography over silica gel eluting with ethyl acetate/«-heptane (2:1), afforded the title compound as a white solid (5.5 g, 78 %).MS: M = 482.0 (ESI-)1H-NMR (400 MHz, DMSO): delta (ppm) = 1.28 (s, 6H), 1.34 (t, 3H), 1.46 (s, 9H),4.41 (q, 2H), 4.51 (br, 2H, rotamers), 4.60 (br, 2H, rotamers), 7.42 (m, IH), 7.47 (s, IH), 7.71 (m, IH), 10.58 (s, IH), 11.45 (s, 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; F. HOFFMANN-LA ROCHE AG; WO2008/17465; (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. 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 15366-34-4

To a mixture of tert-butyl 3-(methanesulfonyloxy)azetidine-l-carboxylate (750 mg, 2.98 mmol) in DMF (10 mL) was added K2C03(1.2 g, 8.95 mmol) and methyl lH-pyrazole- 3-carboxylate (376.4 mg, 2.98 mmol). The reaction was stirred at 100 C overnight. TLC showed the reaction was complete. The mixture was washed with water and extracted with EA. The organic layer was dried over anhydrous Na2S04and concentrated under reduced pressure to give methyl l-(l-(tert-butoxycarbonyl)azetidin-3-yl)-lH-pyrazole-3-carboxylate (650 mg). LC-MS (ESI) found: 236 [M+H-56]+.

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; ZAFGEN, INC.; ZAHLER, Robert; VATH, James, E.; (239 pag.)WO2019/118612; (2019); 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. 129768-28-1, name is 5-(Trifluoromethyl)-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C5H3F3N2O2

3-(Trifluoromethyl)-1H-pyrazole-5-carboxylic acid (Intermediate 15) (1.30 g, 7.20 mmol) was dissolved in acetonitrile (20 ml_), CDI (1.40 g, 8.66 mmol) was added portion-wise and the resulting mixture was stirred at room temperature for 2 h. Potassium 3-ethoxy-3-oxopropanoate (Intermediate 16) (1.22 g, 7.20 mmol) and MgCI2(823 mg, 7.20 mmol) were then added and the resulting reaction mixture was stirred at room temperature for 14 h. The mixture was concentrated in-vacuo, the residue was partitioned between H20 (40 ml_) and EtOAc (30 ml_) and the layers were separated. The aqueous layer was further extracted with EtOAc (2 x 30 ml_), the combined organic layers were dried (Na2S04) and the solvent was removed in-vacuo. The crude product was purified by triturating with pentane (decanting off the solvent) and dried under high vacuum to give ethyl 3-oxo-3-(3- (trifluoromethyl)-1H-pyrazol-5-yl)propanoate (1.20 g, 67 %) as a gum.LCMS (System 2, Method E): m/z 249 (M-H) (ESI -ve), at 4.47 min, 241 nm.

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; HEPTARES THERAPEUTICS LIMITED; BROWN, Giles; CONGREVE, Miles; TEOBALD, Barry; FIELDHOUSE, Charlotte; SWAIN, Nigel; PICKWORTH, Mark; BOTTEGONI, Giovanni; (109 pag.)WO2020/79457; (2020); A1;,
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 27258-32-8 as follows. Recommanded Product: 27258-32-8

17. Preparation of 3-difluoromethyl-1-methylpyrazole from 1-methylpyrazole-3-carbaldehydeAt -20° C., (diethylamino)sulfur trifluoride (DAST, 87.8 g, 0.54 mol) was added dropwise to a solution of 1-methylpyrazole-3-carbaldehyde (20 g, 0.18 mol) in methylene chloride (200 ml). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then added carefully to ice/water (400 g) and extracted twice with methylene chloride (100 ml each). The combined organic phase was washed twice with water (100 ml each) and twice with NaCl solution (100 ml each) and dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was separated by fractional distillation. 3-Difluoromethyl-1-methylpyrazole (16.5 g, transition temperature 141° C. at 570 mbar) was isolated in a purity of 95percent. This corresponds to a yield of 66.8percent.

According to the analysis of related databases, 27258-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; US2010/174094; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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. category: pyrazoles-derivatives

General procedure: To a stirred solution of N,N?-Di-Boc-1H-pyrazole-1-carboxamidine (1.61 mmol) in dry THF, Ph3P(1.42 mmol) and the appropriate alcohol (2.10 mmol) were added under N2 atmosphere. The solutionwas cooled at 0 C and DIAD (2.42 mmol) was added dropwise. The reaction mixture was stirred atreflux for 16 h. The solvent was evaporated and DCM and water were added. Organic phase wasseparated and the aqueous layer was extracted with DCM. The residue was purified by flashchromatography (Hexane/AcOEt 9:1) affording desired compound.

The synthetic route of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maccari, Giorgio; Deodato, Davide; Fiorucci, Diego; Orofino, Francesco; Truglio, Giuseppina I.; Pasero, Carolina; Martini, Riccardo; De Luca, Filomena; Docquier, Jean-Denis; Botta, Maurizio; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3332 – 3336;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics