Category: pyrazoles-derivatives

Reference of 3920-50-1,Some common heterocyclic compound, 3920-50-1, name is Pyrazole-3-carboxaldehyde, molecular formula is C4H4N2O, 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.

1.04 g (15 mmol) of hydroxylamine hydrochloride, 1.23 g (15 mmol) of sodium acetate and 40 ml of ethanol were added to a 100 ml three-necked flask, and 0.96 g (10 mmol) of 3-formalpyrazole was added thereto with stirring.The temperature was raised to 60 C and the reaction was carried out for 3 h. After the reaction, the milky white turbid liquid was obtained and cooled to room temperature.filter,The filtrate was evaporated to give an oily viscous solid, which was dissolved in 50 ml of water.Extract 50 times with 50 ml of ethyl acetate.The organic phase was dried over anhydrous sodium sulfate and filtered.The filtrate was evaporated to dryness to give a pale yellow viscous solid 0.99 g.The yield was 89.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazole-3-carboxaldehyde, its application will become more common.

Reference:
Patent; Xi’an Modern Chemical Institute; Zhang Yiying; Li Purui; Zhou Cheng; Wang Wei; Sun Chenghui; (7 pag.)CN109438353; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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.

Intermediate 15 2,5-dichloro-N-(5-cvclopropyl-lH-pyrazol-3-yl)pyrimidin-4-amine [0096] A mixture of 5-cyclopropyl-lH-pyrazol-3-amine (246 mg, 2.00 mmol), 2,4,5-trichloropyrimidine (367 mg, 2.00 mmol, 1 equiv.) and Na2CO3 (233 mg, 2.20 mmol, 1.1 equiv.) in EtOH (10 mL) was heated at 40 0C for 16 h. The crude reaction mixture was diluted with EtOAc and sequentially washed with: water (3x) and saturated aqueous NaCl (Ix). The resulting EtOAc layer was dried over Na2SO4 and then concentrated in vacuo, providing 2,5-dichloro-N-(5-cyclopropyl-lH-pyrazol-3- yl)pyrimidin-4-amine; ESMS m/z 270.0 (M + H+).

The synthetic route of 175137-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1018446-95-1,Some common heterocyclic compound, 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, molecular formula is C8H13N3O2, 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.

(C) 1-(2-(2-(2-((1H-Pyrazol-4-yI) amino) -5-methylpyrimidin-4-yI) ethyl)phenyl) cyclopropanecarboxamide (46)A mixture of 1-(2-(2-(2-chloro-5-methylpyrimidin-4-yl)ethyl) phenyl)cyclopropanecarboxam ide A40 (0.147 g, 0.465 mmol), teit-butyl 4- amino-i H-pyrazole-1-carboxylate (0.102 g, 0.559 mmol), 052003 (0.455 g, 1.40 mmol), Xantphos (0.011 g, 0.019 mmol) and Pd(OAc)2 (0.002 g, 0.009 mmol) in 1,4- dioxane (5 mL) was bubbled with N2 for 10 minutes before being heated in themicrowave for 20 minutes at 120 00 The reaction mixture was cooled to room temperature, adsorbed onto silica, and purified by column chromatography (Biotage Isolera, 24 g Si02 cartridge, 20-100% EtOAc in petroleum benzine 40-60 00 then 0- 20% MeOH in EtOAc) to give a white solid. This solid was taken up in DCM and precipitated by the addition of cyclohexane. The suspension was sonicated for 10minutes and the precipitate was isolated by vacuum filtration and washed with Et20 to give the title compound 46 as a white solid (0.021 g, 12%). LCMS-D: rt 2.98 mm; m/z 363 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); 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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 176969-34-9

Add a 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (30.0 mmol) and 10 mL of sulfoxide to a 100 mL reaction flask, and heat to reflux. After waiting for the reaction solution to change from turbid to clear, continue to react for 30 minutes.Stop heating and concentrate to remove excess sulfoxide,1-methyl-3-difluoromethyl-1H-pyrazole-4-formyl chloride represented by the formula (V-1) was obtained, and it became a solid after cooling.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Liu Xinghai; Guo Changfei; Jin Tao; Tan Chengxia; Weng Jianquan; Wu Hongke; (20 pag.)CN110615765; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 69843-13-6, 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. 69843-13-6, name is 1-Methyl-1H-pyrazol-4-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 34 6-[3-(4-Chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-N-(l-methyl-lH-pyrazol-4-yl)- nicotinamide To a solution of 6-[3-(4-chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (224 mg, 0.65 mmol) and 1 -methyl- lH-pyrazol-4-ylamine (0.65 mmol) in THF (6 mL) at 0 C were added 1-hydroxybenzotriazole hydrate ( 100.8 mg, 0.65 mmol), N-ethyldiisopropylamine (281.7 mu?, 1.613 mmol) and N-(3-dimethylaminopropy)-N -ethylcarbodiimidazole hydrochloride (126.2 mg, 0.65 mmol). The resulting reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (Si02, heptane:ethyl acetate = 3: 1 to 1:4) afforded the title compound (201 mg, 73%) which was obtained as a white solid. MS: m/e = 424.2 [M+H]+.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; HANLON, Steven Paul; HILDBRAND, Stefan; IDING, Hans; THOMAS, Andrew; WALDMEIER, Pius; WO2013/57123; (2013); 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. 121507-34-4, name is 5-Isopropoxy-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H11N3O

To a mixture of 2,3,6-trichloro-5-nitropyridine (2.61 g, 11.4 mmol) and DIEA (1.90 ml, 11.4 mmol) in THF (50 ml) was added 5-isopropoxy-l/J-pyrazol-3-amine (1.20 g, 8.50 mmol) at 0 0C. After addition, the reaction mixture was stirred at 25 C for 5 days. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane-EtOAc = 1 : 1) to give the title compound as a yellow solid (0.51 g, 18%). 1H NMR (400 MHz) delta 12.22 & 11.35 (s, IH), 10.12 & 9.80 (s, IH), 8.64 & 8.54 (s, IH), 5.95 & 5.84 (s, IH), 4.70 & 4.46 (m, IH), 1.27-1.32 (m, 6H). MS: Calcd.: 331; Found: [M+H]+ 332.

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; WO2006/87538; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

2458-26-6, name is 3-Phenyl-1H-pyrazole, 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 3-Phenyl-1H-pyrazole

6.15. Synthesis of (S)-2-Amino-3-[4-(2-amino-6-{2,2,2-trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethoxy}-pyrimidin-4-yl)-phenyl]-propionic acid 2,2,2-Trifluoro-1-(2-iodo-phenyl)-ethanol (0.331 g, 1.1 mmol), 3-phenyl pyrazole (0.144 g, 1.0 mmol), CuI (0.019 g, 0.1 mmol), K2CO3 (0.290 g, 2.1 mmol), (1R,2R)-N,N’-dimethyl-cyclohexane-1,2-diamine (0.028 g, 0.2 mmol) and toluene (10 ml) were taken in a 20 ml pressure tube and the mixture was heated at 130 C. (oil bath temperature) for 12 h. The mixture was diluted with ethyl acetate and washed with H2O (2*20 ml), brine, and dried over sodium sulfate. Removal of solvent gave a crude product, which was purified by ISCO column chromatography using 5-10% ethyl acetate in hexane as solvent to afford 2,2,2-trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethanol (75 mg).

The synthetic route of 2458-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jin, Haihong; Shi, Zhi-Cai; Tunoori, Ashok; Wang, Ying; Zhang, Chengmin; Devasagayaraj, Arokiasamy; US2008/153852; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31230-17-8,Some common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

Compound 2a (3.32 g, 20 mmol), 3-amino-5-meth- ylpyrazole (1.94 g, 20 mmol) and diisopropylethylamine (5.17 g 40 mmol) were added to a solution of2O mE of ethanol and then stirred at room temperature for 2 days. The insoluble substance was collected to obtain Compound 2b (3.9 g. Yield86percent), MS [M+1] 228.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Patent; ZHEJIANG HISUN PHARMACEUTICAL CO., LTD.; Ding, Yili; Yang, Xuan; Yan, Qingyan; Bai, Hua; Cai, Lifeng; Smith, Kenneth; Chai, Jian; US2014/378488; (2014); 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. 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

In an autoclave, 10 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde were dissolved in 150 ml of ethanol, and 10.4 g of triethylamine and 500 mg of 5% palladium on calcium carbonate were added. The autoclave was flushed with nitrogen and subsequently pressurised to 5 bar hydrogen. The reaction mixture was then stirred at 30 C. for 4 h. After filtration of the catalyst, the solvent was removed under reduced pressure and the product was obtained as a solid (7.4 g) having a melting point of 46-47 C. 1H NMR (CDCl3) 4.1 (s, 3H), 6.85 (t, 1H), 7.73 (s, 1H), 10.1 (s, 1H) ppm.

The synthetic route of 660845-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pazenok, Sergii; Lui, Norbert; Mueller, Thomas Norbert; US2015/126748; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 578008-32-9, A common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, molecular formula is C9H15N3O2, 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.

Step D: To 4-chloro-2-[difluoro-(5-fluoro-pyridin-2-yl)-methyl]-8-bromo-quinazoline (0.19 g, 0.49 mmol) in DMA (1.0 mL) were added 3-amino-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.30 g, 1.53 mmol) and HOAc (0.065 mL, 1.1 mmol) and the mixture was heated to 100 C. for 5 h. The mixture was allowed to cool to rt and purified by reverse phase HPLC (ammonium acetate modifier). Fraction 1 containing pure product was treated with saturated aq NaHCO3 (2-4 mL) and concentrated under reduced pressure. The aqueous residue was extracted with DCM (3×30 mL) and the combined extracts were washed with sat aqueous NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure to afford 8-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine (48 mg, 20%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 12.22 (br s, 1H), 10.87 (br s, 1H), 8.57-8.81 (m, 2H), 8.24 (d, J=7.5 Hz, 1H), 8.02 (d, J=5.3 Hz, 2H), 7.54 (t, J=7.9 Hz, 1H), 5.95 (s, 1H), 2.17 (s, 3H); LC-MS (ESI) m/z 449/451 (M+H+).

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; Hadd, Michael J.; Holladay, Mark W.; Rowbottom, Martin; US2012/53174; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics