Category: pyrazoles-derivatives

Application of 1572-10-7, These common heterocyclic compound, 1572-10-7, name is 3-Amino-5-phenylpyrazole, 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: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.

The synthetic route of 1572-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin; Chinese Chemical Letters; vol. 31; 2; (2020); p. 418 – 422;,
Pyrazole – Wikipedia,
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Reference of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-iodo-1-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles)and sodium carbonate (27.98 gm, 0.264 moles) wereadded. The reaction mixture was evacuated and backfihled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted withethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60-70C, cooled the mixture to 20-30C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30C. The solid product obtained was filtered, washedwith cold Dl water (100 ml) and dried at 40-50C to afford the product, I-Methyl-IHpyrazole-4-carbonitrile.Drywt : 17.94gmYield : 0.32 w/w (63%);

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, 4-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M.; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2109; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

3994-50-1, name is 1-Methyl-4-nitro-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. Recommanded Product: 1-Methyl-4-nitro-1H-pyrazole

Intermediate 153 (Z)-1-(1-Methyl-4-nitro-1H-pyrazol-5-yl)cyclohept-4-enol To a solution of 1-methyl-4-nitro-1H-pyrazole (1.5 g, 11.8 mmol) and (Z)-cyclohept-4-enone (1.4 g, 13.0 mmol) in dry THF (30 mL) under nitrogen cooled to -78 C. was added dropwise a solution of lithium hexamethyldisilazide (1.0 M in THF, 30 mL, 29.5 mmol). The reaction mixture was allowed to warm to -40 C. and stirred for 90 min. Saturated aqueous ammonium chloride solution (30 mL) was added (dropwise initially) and the mixture was allowed to warm to room temperature and extracted with EtOAc (150 mL). The organic layer was washed with water (30 mL), washed with brine (20 mL), separated, dried over MgSO4 and concentrated under reduced pressure. Purification via silica gel column chromatography (20-25% EtOAc) gave (Z)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)cyclohept-4-enol as a tan oil (1.37 g, 49%).

The synthetic route of 3994-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Genentech, Inc.; Burch, Jason; Sun, Minghua; Wang, Xiaojing; Blackaby, Wesley; Hodges, Alastair James; Sharpe, Andrew; US2014/88117; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-20-0, name is 1-Methyl-1H-pyrazole-3-carboxylic acid, 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 25016-20-0, Recommanded Product: 25016-20-0

General procedures for Example 59-76; A 4mL scintillation vial was charged with a stir bar, a solution of 59a (12.22 mg, 0.018mmol) dissolved in 1 mL of Nu,Nu-dimethylacetamide, a solution of carboxylic acid monomer (1.20 eq, 0.022 mmol) dissolved in 2.0mL of Nu,Nu-dimethylacetamide, a solution of HATU (8.36 mg, 1.20 eq, 0.022 mmol) dissolved in 500 mu^ of Nu,Nu-dimethylacetamide, and triethylamine (5.14muEpsilon, 2.0 eq, 0.036mmol). The vial was capped using inserts followed by Synthos caps. The vials were placed in Synthos Anton-Parr microwave optimizer at 150C for 30 minutes. The crude mixture was checked via LCMS for completion and concentrated to dryness. The residue was then dissolved in 1.4 mL of DMSO/Methanol (1/1 v:v) and purified through reverse phase HPLC to afford pure products recovering between 25-59% yield.HPLC condition: Samples were purified by preparative HPLC on a Phenomenex Luna C8(2) 5 um 100A AXIA column (30mm x 75mm). A gradient of methanol (A) and 0.1%trifluoroacetic acid in water (B) was used, at a flow rate of 50mL/min (0-0.5 min 20% A, 0.5- 6.0 min linear gradient 20-100% A, 6.0-7.0 min 100% A, 7.0-8.0 min linear gradient 100- 10% A).; Example 59; (2R,6S,13aS,14aR,16aS,Z)-N-(cyclopropylsulfonyl)-2-(8-fluoro-3-methylquinoxalin-2- yloxy)-6-(l-methyl-lH-pyrazole-3-carboxamido)-5,16-dioxo- 1,2,3,5,6,7,8,9,10,11,13a, 14,14a, 15,16, 16a-hexadecahydrocyclopropa[e]pyrrolo[l, 2- a][l,4]diazacyclopentadecine-14a-carboxamide; The title compound 59 was prepared according to the general procedure used for Example 59-76 using l-methyl-lH-pyrazole-3-carboxylic acid as the carboxylic acid monomer. MS (ESI): m/z = 737.2 [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-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; ENANTA PHARMACEUTICALS, INC.; CHEN, Hui-ju; MCDANIEL, Keith, F.; GREEN, Brian, E.; SHANLEY, Jason, P.; KRUGER, Albert, W.; GANDARILLA, Jorge; WELCH, Dennie, S.; CINK, Russell, D.; GAI, Yonghua; WANG, Guoqiang; OR, Yat, Sun; WO2011/156337; (2011); A2;,
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. 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 345637-71-0

To a solution of (5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O- (benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1 M HCI solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10: 1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)- acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester (13.6 g, 88 %). 1 H-NMR (400 – -MHz, CDCI3): delta = 1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1 H), 3.22-3.43 (m, 1 H), 4.03-4.12 (m, 1 H), 4.42 (q, 3H), 4.54-4.69 (m, 1 H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1 H), 8.10 (br, 1 H). MS: m/z = 209 (M+1).

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 345637-71-0.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SULZER-MOSS, Sarah; LAMBERTH, Clemens; RESPONDEK, Mathias, Stephan; QUARANTA, Laura; CEDERBAUM, Fredrik; BERTHON, Guillaume; WO2012/69633; (2012); 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. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Diethyl 3,5-pyrazoledicarboxylate

Crude 2-chloro-l-(l-(4-methoxybenzyl)-lH-pyrazol- 4-yl)ethanone (7.1 g, 21 mmol) was dissolved in acetonitrile (100 mL). Diethyl lH-pyrazole-3,5- dicarboxylate (4.6 g, 21 mmol) was added, followed by K2CO3 (5.9 g, 43 mmol), and the reaction mixture was stirred at 45 C for 1 h. The reaction mixture was cooled to ambient temperature, diluted with EtOAc, filtered, and concentrated. The residue was purified over silica gel to afford the title compound (8.7 g, 92% yield) as a white solid

According to the analysis of related databases, 37687-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5334-43-0,Some common heterocyclic compound, 5334-43-0, name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile, molecular formula is C10H8N4, 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: Equimolar portionsof the intermediate compounds 1 (1 mmol) and the intermediatecompounds 3 (1 mmol) were dissolved in approximately 8 mL ofethanol. The reaction solution was allowed to stir at 80 8C for 2 huntil the reaction was complete. The reaction was monitored byTLC. Mostly, a precipitate formed and was then collected by suctionfiltration.

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-phenyl-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,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 13808-64-5, A common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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.

A solution of potassium tert-butoxide (IM in THF, 18ml) was added to a solution of 4-bromo- 3-methylpyrazole (2.9Ig) in THF (20ml). The mixture was stirred at RT for 20min then dimethylsulfamoyl chloride (1.94ml) was added and stirred overnight. The solvent was evaporated under reduced pressure and the residue purified by chromatography on silica eluting with 20% ethyl acetate/isohexane.1 H NMR DMSO-d6: delta 8.47 (IH, s), 2.85 (6H, s), 2.23 (3H, 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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/37982; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 20583-33-9,Some common heterocyclic compound, 20583-33-9, name is 1-(1H-Pyrazol-3-yl)ethanone, 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.

To a solution of 1-(1H-pyrazol-3-yl)ethan-1-one (14-S1, 1 equiv) in CH3CN (10 vol) was added tert-butyl 2-bromoacetate (14-S2, 1.1 equiv) and potassium carbonate (1.1 equiv). The mixture was refluxed overnight under an atmosphere of argon. After cooling the reaction mixture to room temperature, the mixture was filtered through Celite and washed with CH3CN. The filtrate was concentrated under reduced pressure and the remaining residue was purified by column chromatography on silica gel (eluted with DCM/EtOAc) to afford compound 14-S3.

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

Reference:
Patent; ACHILLION PHARMACEUTICAL, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel Charles; GREENLEE, William; EASTMAN, Kyle J.; (0 pag.)WO2018/160891; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1572-10-7, 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 1572-10-7 as follows.

General procedure: The corresponding amine (10 mmol) and aldehyde (20 mmol) were dissolved in absolute ethanol (40 mL) and a catalytic amount of acetic acid added. The mixture was refluxed for 72 h. The crude product was isolated from the reaction solution by precipitation with diethyl ether and recrystallization from hot methanol.

According to the analysis of related databases, 1572-10-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Adamski, Ariel; Kruszka, Dariusz; Dutkiewicz, Zbigniew; Kubicki, Maciej; Gorczy?ski, Adam; Patroniak, Violetta; Tetrahedron; vol. 73; 24; (2017); p. 3377 – 3386;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics