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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C6H8N2O

In a sealed tube, under N2, 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (284 mg; 2.28mmol) and Ti(iPrO)4 (727 jiL; 3.05 mmol) were added to a solution of intermediate 11(500 mg; 1.52 mmol) in THF (10 mL). The solution was stirred at 50C for 2h. Thereaction mixture was cooled to 5C and iPrMgCl (3.8 mL; 7.61 mmol) was addeddropwise. The reaction mixture was allowed to rise slowly to rt and stirred overnight. The reaction mixture was poured onto a 10% aqueous solution of K2C03 and EtOAc. The insoluble was filtered through a pad of celite then, the organic layer was decanted, dried over MgSO4, filtered and the solvent was evaporated. The residue (866 mg, brownoil) was purified by chromatography over silica gel (Si02 40 g; eluent: from 96% DCM,4% MeOH, 0.4% NH4OH to 93% DCM, 7% MeOH, 0.7% NH4OH). The pure fractionswere collected and the solvent was evaporated to dryness. The residue (496 mg, yellow oil) was recrystallized with diethylether. The precipitate was filtered and dried to give324 mg of compound 161( (45%, white solid).

The synthetic route of 25016-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (2018); A1;,
Pyrazole – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, SDS of cas: 930-36-9

Phosphorus oxychloride (6.92 g, 45.1 mmol, 1.50 equiv.) was cooled to 0 0C and then added drop-wise to anhydrous DMF (3.50 mL, 45.2 mmol, 1.50 equiv.) at 0 0C. The mixture was stirred 1 hour at room temperature and was then heated to 80 0C. The compound of formula VIII (2.50 mL, 30.2 mmol) was then added drop-wise to the reaction, and the resulting mixture was stirred 3 hours at 95 0C. The reaction was then quenched by slow addition to ice (40 g). The pH of the resulting solution was 2, and it was raised to 5 by slow addition of 12N aqueous sodium hydroxide solution (11.2 mL). The resulting aqueous solution was extracted with dichloromethane and/or ether (7 x 40 mL), and additional sodium hydroxide was added during extraction, as needed, to maintain a pH of 5. The extracts were then combined, dried over sodium sulfate, filtered and concentrated to yield a brown oil (3.79 g, 59% yield).

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; SCHERING CORPORATION; WO2008/153870; (2008); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, 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. Product Details of 42027-81-6

To a stirred solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol 17 (2.0 g, 1.23 mmol) in EtOH (25 mL), 0.40 g of Pd(OH)2 added and then stirred reaction under H2 gas atm for 1 4h. After the completion of reaction (TLC monitoring) the reaction mixture was filtered through celite bed, washed with MeOH, concentrated the solvent and the crude compound was purified by triturating with ether and pentane to give 2-(4-amino-1H- pyrazol-1-yl)ethanol precursor-07 as brown solid (1.30 g, 81% yield). MS: 128.07 (M+H).

The synthetic route of 42027-81-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
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Synthetic Route of 25016-20-0, 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. 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 67;(i?)-(l-Methyl-l/-r-pyrazoI-3-yl)(l-(4-(trifluoromethyl)phenyl)-3,4-dihydroiso- quinoIin-2(lH)-yl)methanone; A solution of (R)- -(4-(trifluoromethyl)phenyl)- 1,2,3, 4-tetrahydroisoquinoline (58 mg, 0.21 mmol, example 30, step 1) in DMF (1 mL) was added 1-methyl-leta- pyrazole-3-carboxylic acid (Fluorochem, 34 mg, 0.27 mmol), 1-hydroxybenzo- triazole hydrate (42 mg, 0.27 mmol), and JV-((isopropylimino)methylene)propan- 2-amine (66 muL, 0.42 mmol). The resulting mixture was then stirred at RT for 16 h. Then, the mixture was filtered and the filtrate was purified by preparative HPLC to give the target compound. The product was dissolved in MeOH and passed through PL-HCO3 MP resin and the resin was washed with MeOH (2 x 0.3 mL). The combined filtrates were concentrated and dried under vacuum to give the title compound as a light-yellow solid. MS (ESI, positive ion) m/z: 386 (M+H).

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; WO2009/73203; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 34091-51-5, name is 5-Iodo-1-methyl-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. Recommanded Product: 34091-51-5

Production Example 11 1′-(4-Fluorophenyl)-2-methyl-1’H,2H-3,4′-bipyrazole Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (600 mg), [1-(4-fluorophenyl)-1H-pyrazol-4-yl]boronic acid (650 mg), tetrakistriphenylphosphine palladium (166 mg), 2 M sodium carbonate aqueous solution (2.9 mL), ethanol (3.0 mL) and toluene (6.0 mL) was stirred at 100 C. for 4 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was concentrated under a reduced pressure, and the residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to ethyl acetate), so as to obtain the title compound (450 mg) in the form of a light yellow solid. 1H NMR (600 MHz, CHLOROFORM-d) delta ppm 3.97 (s, 3H) 6.34 (d, J=1.83 Hz, 1H) 7.14-7.22 (m, 2H) 7.46-7.53 (m, 1H) 7.66-7.72 (m, 2H) 7.83 (s, 1H) 7.98 (s, 1H); MS (ESI pos.) m/z: 243 [M+H]+

The synthetic route of 5-Iodo-1-methyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Nakamura, Toshio; Sakagami, Kazunari; Konishi, Kazuhide; Yamamoto, Kanako; Masuda, Seiji; Matsuda, Yohei; Okada, Kumiko; Shibata, Tsuyoshi; Ohta, Hiroshi; Yasuhara, Akito; Kawamoto, Hiroshi; Amada, Hideaki; Urabe, Hiroki; Nishikawa, Rie; Kashiwa ASHIWA, Shuhei; US2013/137865; (2013); A1;,
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Related Products of 113100-53-1,Some common heterocyclic compound, 113100-53-1, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C6H5F3N2O2, 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 suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.41 mmol) and 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (0.087 g, 0.45 mmol), and pyridine (0.15 mL, 1.83 mmol in acetonitrile (5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.60 mL, 1.02 mmol). The sealed tube was heated to 100 C. for over night and the precipitation formed. After cooling, the precipitate was collected by filtration and washed with cold 1:1 acetonitrile/water to give 1-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (0.120 g, 70%). 1H NMR (400 MHz, DMSO-d): delta 12.61 (bs, 1H), 10.19 (s, 1H), 8.76 (s, 1H), 7.74 (m, 1H), 7.69 (dd, 1H, J=8.4, 2.0 Hz), 7.50 (s, 1H), 6.90 (d, 1H, J=8.0 Hz), 4.00 (s, 3H), 2.92 (t, 2H, J=7.2 Hz), 2.48 (partial masked under d-DMSO, m, 2H); MS (ESI): Calcd. For C18H14F3N5O2S: 421, found 422 (M+1)+.

The synthetic route of 113100-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); A1;,
Pyrazole – Wikipedia,
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4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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. category: pyrazoles-derivatives

General procedure: A mixture of substituted 3-(2-aryl-2-oxoethylidene)indolin-2-one 1 (1 mmol), 1,3-dimethylurea (2, 1.2 mmol) or 5-amino-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (4, 1 mmol), PTSA·H2O (0.3 mmol), and MeCN (5 mL) was added to a 25 mL flask and reacted at 80 C (monitored by TLC) about 2 h. After completion, the mixture was cooled to r.t. and the precipitate obtained was isolated by filtration and drying. Compounds 3 or 5 were purified by recrystallization (DMF or EtOH).

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dai, Lei; Shu, Ping; Wang, Zhansheng; Li, Qingyang; Yu, Qiuyu; Shi, Yanhui; Rong, Liangce; Synthesis; vol. 49; 3; (2017); p. 637 – 646;,
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Synthetic Route of 18213-75-7, A common heterocyclic compound, 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, molecular formula is C5H8N4O, 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.

Isopropyl chloroformate (1.95 g, 14.3 mmol) and N-methylmorpholine (1.44 g, 14.3 mmol) were added to a solution of 4,4,4-trifluorobutanoic acid (2.03 g, 14.3 mmol) in THF (40 mL) at -15C. The solution was stirred for 10 min then cooled to -50C and a solution of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (2.0 g, 14.3 mmol) and DIEA (2.49 ml, 14.3 mmol) in DMF (20 ml) was added. The solution was allowed to slowly warm to ambient temperature over 2 h. The solution was diluted with EtOAc and washed with brine. The organic layer was dried, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography using 0% to 15% MeOH in CH2CI2 gradient to give the title compound.

The synthetic route of 18213-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAN, Xiaoqing; WHITEHEAD, Alan; RAGHAVAN, Subharekha; CERNAK, Timothy, A.; DREHER, Spencer; GROEPER, Jonathan; GUO, Jian; ZHANG, Yong; WO2015/88886; (2015); A1;,
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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. 876343-24-7, name is 1-Ethyl-1H-pyrazol-4-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Ethyl-1H-pyrazol-4-amine

EXAMPLE 187: 4-[4-(l-EthyMNo.-pyrazol-4-ylamino)-7No.-pyrroIo[2,3-“npyrimidin-6-yI]-3,6-dihydro-2No.-pyridine-l-carboxylic acid fcrf-butyl ester.; [527] A mixture of 4-(4-chloro-7No.-pyrrolo[2,3 -d]pyrimidin-6-yl)-3 ,6-dihydro-2No.-pyridine-1-carboxylic acid fert-butyl ester (HOmg, 0.33mmol) and l-ernyl-4-amino-l./:/’-pyrazole (44mg, 0.39mmol) in 1-butanol (3mL) was heated at 120°C overnight, LC-MSshowed the desired product and some de-Boc product. After the mixture was cooled to rt, itwas diluted with methylene chloride (3mL), then AyV-diisopropylethylamine (0.1 ImL,0.66mmol) and di-tert-butyldicarbonate (72mg, 0.33mmol) were added, the resulting mixturewas stirred at rt for 30min. The mixture was diluted with EtOAc (30mL), then washed withbrine (20mL), and dried over anhydrous sodium sulfate. The solvent was evaporated underreduced pressure, and the residue was crystallized with EtOAc to give, the title compound asan off-white solid. LC-MS (ES, Pos.): 410 [MH*]. ‘HNMR (CDC13, 400 MHz): 8 = 1.51 (s,9H), 1.56 (t, J = 7.3 Hz, 3H), 2.50 (m, 2H), 3.66 (m, 2H), 4.16 (m, 2H), 4.22 (q, J = 7.3 Hz,2H), 6.04 (s, 1H), 6.17 (s, 1H), 6.57 (s, 1H), 7.56 (s, 1H), 7.95 (s, 1H), 8.38 (s, 1H), 10.96 (brs, 1H).

The synthetic route of 876343-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 3398-16-1, 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. 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a dry three-necked flask with a magnetic rotor was added 4-bromo-3,5-dimethylpyrazole (3.5714 g, 20 mmol, 98%, 1.0 eq.), phenylboronic acid (2.9552 g, 24 mmol, 99%, 1.2 equivalents),Palladium acetate (0.1123 g, 0.5 mmol, 0.025 equivalent), ligand S-Phos (0.5027 g, 1.2 mmol, 98%, 0.06 equivalent), 1,4-dioxane (60 mL) and potassium carbonate (8.2920 g, 60 mmol, 3.0 eq.) of aqueous solution (20 mL).Nitrogen was bubbled for 15 minutes and then the reaction flask was placed in a 115 C oil bath.After stirring for 15 hours, the reaction was monitored by thin layer chromatography. It was cooled to room temperature and extracted with dichloromethane (20 mL×3).All organic phases were combined and dried over anhydrous sodium sulfate.Filtration, concentration, and purification of the crude product by flash chromatography on silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 3/1 – 1/2) to give 3,5-dimethyl-4-phenyl -1H-imidazole,The white solid was 3.0773 g, and the yield was 89%.

The synthetic route of 4-Bromo-3,5-dimethylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Ruisheng Optoelectric Science And Technology (Changzhou) Co., Ltd.; Li Guijie; Dai Jianxin; She Yuanbin; Chen Shaohai; (127 pag.)CN108659050; (2018); A;,
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