Tag: M.W:200-300

These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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. Computed Properties of C7H7F3N2O2

(S)-Benzyl 5-(hydroxymethyl)-2,3-dihydro-7/-/-inden-2-ylcarbamate (2.96 mmol, 880mg) was dissolved in DCM (10 ml.) and thionyl chloride (5.92 mmol, 0.432 ml, 704 mg) added. The mixture was stirred at room temperature for 30 min TLC before the solvent was removed under reduced pressure and residual thionylchloride azeotroped with DCM (x3). To the residue was added potassium carbonate (8.88 mmol, 1227 mg) followed by DMF (8 ml) then ethyl 3-(trifluoromethyl)-7/-/-pyrazole-4-carboxylate (2.96 mmol, 616 mg) and the mixture heated to 60 0C. After 1 h the mixture was concentrated and partitioned between EtOAc/H2O and the organic layer was washed with water (x 3). The organic layer was dried, filtered and concentrated to give a yellow oil which was purified by flash chromatography eluting with 15% EtOAc/Heptane to give the desired isomer as a colourless oil (45 mg, 0.092 mmol, 3.1%). 1H NMR (400 MHz, CDCI3) delta 1.34 (t, 3H) 2.75 (m, 2H) 3.25 (m, 2H) 4.33 (q, 2H), 4.50 (m, 1 H) 4.95 (m, 1 H), 5.08 (s, 2H) 5.48 (s, 2H) 7.00 (m, 2H) 7.15 (d, 1 H) 7.34 (m, 5H) 7.99 (s, 1 H).

The synthetic route of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); 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. 138907-68-3, name is Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 138907-68-3

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

According to the analysis of related databases, 138907-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
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Synthetic Route of 37687-24-4, 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. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (3.00 g, 14.1 mmol), 2-bromo-1-(8-fluoronaph- thalen-2-yl)ethanone (Intermediate 205A, 3.78 g, 14.1 mmol) and potassium carbonate (2.15 g, 15.6 mmol) in acetone (40 ml) was stirred at RT overnight. After filtering off the solids, the filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic phase was washed with water and brine, then dried over sodium sulfate and concentrated. The crude product was purified by flash-chromatography on silica gel (80 g, eluent: 0-20% ethyl ace- tate in petroleum ether) to give the title compound (4.21 g, 70% of theory, 94% purity). LC/MS [Method 6]: Rt = 1.25 min; MS (ESIpos): m/z = 399 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.85 (s, 1H), 8.22 (d, 1H), 8.14-8.10 (m, 1H), 7.94 (d, 1H), 7.77-7.72 (m, 1H), 7.55-7.50 (m, 1H), 7.39 (s, 1H), 6.46 (s, 2H), 4.33 (q, 2H), 4.24 (q, 2H), 1.32 (t, 3H), 1.18 (t, 3H).

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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; MUeLLER, Steffen; SCHOHE-LOOP, Rudolf; ORTEGA, HERNANDEZ, Nuria; SUeSSMEIER, Frank; JIMENEZ NUNEZ, Eloisa; BRUMBY, Thomas; LINDNER, Niels; GERDES, Christoph; POOK, Elisabeth; BUCHMUeLLER, Anja; GAUGAZ, Fabienne, Zdenka; LANG, Dieter; ZIMMERMANN, Stefanie; EHRMANN, Alexander, Helmut, Michael; GERISCH, Michael; LEHMANN, Lutz; TIMMERMANN, Andreas; SCHAeFER, Martina; SCHMIDT, Georg; SCHLEMMER, Karl-Heinz; FOLLMANN, Markus; KERSTEN, Elisabeth; WANG, Vivian; GAO, Xiang; WANG, Yafeng; (801 pag.)WO2019/219517; (2019); A1;,
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Synthetic Route of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 stirred 0 C solution of tert-butyl 4,6- dihydropyrrolo[3 ,4-c]pyrazole-5 (2H)-carboxylate (100.00 mg, 0.48 mmol) was added lithium bis(trimethylsilyl)amide (1.00 mL, 1.00 mmol) in THF. The mixture was stirred at 0C for 30 mi 2,2-Dimethyloxirane ( 0.29 mL, 2.39 mmol) was added and the mixture was stirred at rt for 3 h and heated to 80 C for 2 h under microwave irradiation. The crude material was diluted with EtOAc, washed with brine (3 x 30 mL), and concentrated under reduced pressure to a yellow oil. The yellow oil was absorbed onto silica and purified (FCC, Si02, 30-70% EtOAc:hexanes) to afford a 1:1 mixture of the title compounds: tert-butyl 2-(2-hydroxy-2-methylpropyl)-4,6-dihydropyrrolo [3,4-c]pyrazole-5(2H)-carboxylate and tenbutyl 1 -(2-hydroxy-2-methylpropyl)-4,6-dihydropyrrolo [3 ,4-c]pyrazole-5 (1 H)-carboxylate (70 mg, 52%).

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 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, Jillian; BOOKSER, Brett; CHEN, Mi; CHUNG, DeMichael; GUPTA, Varsha; HUDSON, Andrew; KAPLAN, Alan; NA, James; RENICK, Joel; SANTORA, Vincent; WO2015/164520; (2015); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic 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 345637-71-0, Recommanded Product: 345637-71-0

A solution of 400 mg (0.77 mmol) of 1,1-dimethylethyl 4-[4-[[methyl[(l/?)-l- phenylethyl]amino]carbonyl]-2-thiazolyl]-l-piperidinecarboxylate (i.e. the product of Example 5, Step A) in 10 mL of a 1:1 mixture of methanol and dichloromethane was treated with 10 mL of 2 N hydrochloric acid in ether and stirred at room temperature for 4 h. The reaction mixture was concentrated on rotary evaporator, and the residue was three times treated with 10 mL of methanol followed by concentration to leave the crude piperidine hydrochloride. The reaction mixture was then dissolved in 10 mL of acetonitrile, and 1.O mL of triethylamine was added. Meanwhile, a solution of 310 mg (1.49 mmol) of 5-methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetic acid in 10 mL of acetonitrile was treated with 1.0 mL of a solution of 1-propanephosphonic acid cyclic anhydride (50 % in ethyl acetate), stirred at room temperature for 15 minutes, then combined with the above amine solution. The reaction mixture was stirred at room temperature overnight, diluted with 50 mL of ethyl acetate, washed with 1 N aqueous hydrochloric acid, 1 N aqueous sodium hydroxide and brine, dried with MgSC^, filtered and concentrated under reduced pressure. Purification by Medium Pressure Liquid Chromatography (MPLC) on silica gel using ethyl acetate/methanol as eluant provided 330 mg of the title product, a compound of the present invention, as a white solid. 1H NMR (CDCl3) delta 1.60-1.80 (m, 5 H), 2.18 (m, 2 H), 2.30 (s, 3H), 2.80 (m, 5 H), 3.27 (m, 2 H), 4.00 (m, IH), 4.95 (s, 2 H), 5.79 and 6.14 (m, total IH), 6.35 (s, IH), 7.37 (m, 5H), 7.84 (s, IH).

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; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/91594; (2008); A2;,
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Pyrazoles – an overview | ScienceDirect Topics

Reference of 1226781-82-3, 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 1226781-82-3 as follows.

Step (4) The distilled pale yellow wet product IV was dissolved in isopropyl acetate 35kg, and then added dropwise with acid solution at roomtemperature (benzenesulfonic acid 7.7kg and 14kg isopropyl acetate), stirring2d, suction filtration to give a pale gray solid, at 40 deg. C vacuum dried togive a pale gray solid after 10h 7.78kg, 95% yield, purity 98.2%.

According to the analysis of related databases, 1226781-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhongshan Yian Tai Pharmaceutical Co., Ltd.; Xu, Liang; Mao, Bo; Huang, Zhihong; Li, Yanxiong; (8 pag.)CN105348286; (2016); A;,
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Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 10250-64-3, A common heterocyclic compound, 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, molecular formula is C11H10N2O2, 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: To a solution of 19 (1.2 eq) and HOBt(1.4 eq) in DMF (0.5 M) were added EDCI (1.3 eq) and a solution of 15a-j or 16a-j (1.0 eq) in DMF (0.25 M), Et3N (3.5 eq) at 0 C. The reaction mixture was stirred at room temperature for 24 hours, then diluted in AcOEt. The organic phase was washed with water twice, saturated aqueous NaHCO3 three times, and brine, then dried over Na2SO4,filtered, and concentrated. The residue was purified by flash column chromatography to give intermediates 17a-j and 18a-j.

The synthetic route of 10250-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 25; 23; (2015); p. 5619 – 5624;,
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Reference of 83-10-3, The chemical industry reduces the impact on the environment during synthesis 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

Step 2) 4-(3-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamide To a suspension of 4-(4-amino-3-chlorophenoxy)picolinamide (191 mg, 0.72 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (168 mg, 0.72 mmol) in DCM (10 mL) was added EDCI (166 mg, 0.86 mmol) and HOAT (20 mg, 0.14 mmol). The reaction was stirred at 46 C. for 6 hours, followed by the addition of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (32 mg, 0.14 mmol) and EDCI (27 mg, 0.14 mmol). The mixture was further stirred at 46 C. for 13 hours, then cooled to rt and diluted with water (10 mL). The resulted mixture was extracted with ethyl acetate (10 mL*3), and the combined organic phases were washed with brine (10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=50/1) to give the title compound as a pale yellow solid (160 mg, 46.5%). MS (ESI, pos. ion) m/z: 478.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6): delta (ppm) 2.71 (s, 3H), 3.37 (s, 3H), 7.19 (m, 1H), 7.23 (m, 1H), 7.43 (m, 3H), 7.50 (m, 2H), 7.60 (m, 2H), 7.72 (s, 1H), 8.13 (s,1H), 8.52 (d, J=5.6 Hz, 1H), 8.63 (d, J=9.1 Hz, 1H), 11.19 (s, 1H).

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, 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wu, Yanjun; Liao, Min; Feng, Yanming; US2015/37280; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, 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 39806-90-1, Formula: C4H5IN2

Step 1: Prepartion of tert-but 4-(l-methyI-lH-pyrazoI-4-yl)-3-oxopiperazine~l- carboxylate: tot-Butyl 3-oxopiperazine-l-carbox late (0.164 g, 0.819 mmol) was suspended in isopropanol (3 mL) under an atmosphere of nitrogen and treated with l-methyl-4-iodo-lH- pyrazole (0.204 g, 0.983 mmol, 1.20 equiv), ethylene glycol (0.051 g, 0.82 mmol, 1.0 equiv). copper iodide (0.03 g, 0.16 mmol, 0.20 equiv), and potassium phosphate (0.695 g, 3.28 mmol, 4.00 equiv), and placed into a preheated oil bath at 100 C for 8 hours. The mixture was cooled to ambient temperature, concentrated in vacuo and the residue was dissolved in dichloromethane, washed with water, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 0: 100 hexanes : ethyl acetate), providing the titled compound.

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; MERCK SHARP & DOHME CORP.; BESHORE, Douglas, C.; KUDUK, Scott, D.; WO2011/137049; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

39806-90-1, name is 4-Iodo-1-methyl-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: 4-Iodo-1-methyl-1H-pyrazole

4-lodo-1-methyl-1H-pyrazole (1.12 g; 5.385 mmol) and 4-(Methoxy-methyl- carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (1.47 g; 5.385 mmol) were dissolved in dry THF (15 mL) under argon. While stirring the clear light yellow solution was cooled down to -60 C and butyllithium (15% solution in n- hexane) (3.72 mL; 5.923 mmol) was added dropwise at this temperature over a period of 10 min. The reaction mixture was stirred for 30 min between -60 and -45 C, then slowly warmed to room temperature and stirred for 14 h. The reaction mixture was cooled to 0 C, quenched with 0% citric acid solution, diluted with ethyl acetate (70 mL) and washed with water and brine, dried with Na2S04) filtered and evaporated to dryness. The oily residue was purified by flash chromatography (Companion RF; 120 g Si50 silica gel column); yield: 999 mg (63%) light green oil (purity: 99.4; Rt: 2.33 min); 1H NMR (500 MHz, DMSO-d6) delta 8.42 (s, 1H), 7.94 (d, J = 0.7 Hz, 1H), 3.97 (d, J = 12.6 Hz, 2H), 3.87 (s, 3H), 3.15 (tt, J = 11.4, 3.6 Hz, 1 H), 2.93 – 2.75 (m, 2H), 1.76 – 1.67 (m, 2H), 1.33-1.46 (m, 1 H); LC/MS (C), Rt: 1.93 min; 238.1 (M+H; BOC-cleaved mass).

The synthetic route of 39806-90-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; DORSCH, Dieter; BUCHSTALLER, Hans-Peter; WO2015/14442; (2015); A1;,
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Pyrazoles – an overview | ScienceDirect Topics