Tag: M.W:200-300

Reference of 2033-45-6, 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. 2033-45-6, name is 3,5-Dimethyl-4-iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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.

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, 3,5-Dimethyl-4-iodopyrazole, other downstream synthetic routes, hurry up and to see.

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

Adding a certain compound to certain chemical reactions, such as: 1226781-82-3, name is tert-Butyl 2-(methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, 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 1226781-82-3, name: tert-Butyl 2-(methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

To the product from Step C (87 g, 303 mmol) in isopropyl acetate (1 L) was added benzensulfonic acid (71.8 g, 454 mmol) and the mixture warmed to 40 C and stirred for 2 h. The mixture was cooled to ambient temperature and stirred for 16 h to give an off-white slurry. The solid was filtered, washed with isopropyl acetate, and suction dried to afford the title compound as a white solid. LC MS: 188.1 (M+l).

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.; HICKS, Jacqueline, D.; BIFTU, Tesfaye; CHEN, Ping; QIAN, Xiaoxia; WILKENING, Robert, R.; WO2011/146358; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1029413-53-3, A common heterocyclic compound, 1029413-53-3, name is tert-Butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate, molecular formula is C12H20N4O2, 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.

Example 72C (1S,2S,3R,4R)-3-{[5-chloro-2-({1-[(3S)-pyrrolidin-3-yl]-1H-pyrazol-4-yl}amino)pyrimidin-4-yl]amino}bicyclo[2.2.1]hept-5-ene-2-carboxamide (+)-(1S,2S,3R,4R)-3-(2,5-Dichloropyrimidin-4-ylamino)bicyclo[2.2.1]hept-5-ene-2-carboxamide (75 mg, 0.25 mmol) and (S)-tert-butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate (63 mg, 0.25 mmol) were combined with 2-propanol (2.4 ml) in a sealed tube and the mixture was heated to 85 C. for 4 hours. The reaction mixture was concentrated to dryness, then treated with 5 mL TFA and stirred for 15 minutes. The mixture was again concentrated to dryness, the residue was dissolved in CH2Cl2, and the mixture was treated with aqueous saturated NaHCO3. The layers were separated and the aqueous layer was further extracted 3* with ethyl acetate. The extracts were dried (Na2SO4) and concentrated, then purified by flash chromatography yielding the desired product. 1H NMR (300 MHz, DMSO-D6) ppm 1.41 (d, J=7.8 Hz, 1H) 1.92-2.04 (m, 1H) 2.07-2.21 (m, 2H) 2.52-2.56 (m, 1H) 2.71-2.91 (m, 3H) 2.93 (d, J=5.4 Hz, 1H) 2.95-3.03 (m, 1H) 3.12 (dd, J=11.5, 7.12 Hz, 1H) 4.13 (t, J=7.5 Hz, 1H) 4.65-4.77 (m, 1H) 6.25-6.40 (m, 2H) 7.25 (s, 1H) 7.51 (s, 1H) 7.61-7.84 (m, 3H) 7.89 (s, 1H) 9.10 (s, 1H); MS (ESI(+)) m/e 415 (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; Abbott Laboratories; US2010/317680; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 155377-19-8, 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. 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3-trifluoromethyl-lH-pyrazole-4-carboxylic acid ethyl ester (2.5 g, 12.0 mmol), copper (I) iodide (0.69 g, 3.6 mmol) and potassium carbonate (3.49 g, 25.3 mmol) in toluene (12 mL) in a round bottom flask was purged with argon. To the reaction mixture was then added iodobenzene (1.61 mL, 14.4 mmol) and racemic trans- N,N’-dimethyl-cyclohexane-l,2-diamine (1.16 mL, 7.2 mmol). The slurry was heated under Ar in an oil bath at HO0C for 24 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered over a bed of celite. The organic washings were combined and concentrated to give a crude which was purified by silica gel chromatography (Isco 120 g column, 0 -> 30% ethyl acetate/hexanes) to give 1- phenyl-3-trifluoromethyl-lH-pyrazole-4-carboxylic acid ethyl ester (2.91 g, 85%) as an off-white solid. The NMR spectrum obtained on the sample is compatible with its structure.

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, Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/141976; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 19968-17-3, 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 19968-17-3 as follows.

To a solution of 4-bromo-3-trifluoromethyl-lH-pyrazole 33 (0.645 g, 3 mmol) in dimethylformamide (DMF) (50 niL) was added NaH (0.2 g, 9 mmol). The mixture was stirred for 0.5 h at room temperature and the 2-bromo-l ,3-thiazole (0.76 g, 4.5 mmol) was added. The reaction mixture was stirred for 1 h at room temperature. The reaction temperature was raised to 90C and stirred for overnight. The reaction was quenched with MeOH and solvent was removed in vacuo. The residue was treated with water and EtOAc. The organic layer was separated and aqueous was extracted with EtOAc. The combined organic phase was dried over Na2S04, filtered, and concentrated to give crude product. The crude product was purified on ISCO columns. Fractions containing pure product were combined and evaporated to give 34 as a brown oil (0.45 g, 50%).

According to the analysis of related databases, 19968-17-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALCIMEDICA, INC.; WHITTEN, Jeffrey, P.; CAO, Jianguo; WANG, Zhijun; GREY, Jonathan; ROGERS, Evan; WO2015/54283; (2015); 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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H15N3O2

4,6-Dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester(0.30 g, 1.43 mmol) was dissolved in tetrahydrofuran (10 mL).Nitrogen protection, sodium hydride (0.11 g, 2.85 mmol, 60%) was added at 0 C.Slowly rise to room temperature for 1 hour, then cool to 0 C,Add 5-methylthiophene-2-sulfonyl chloride (0.39 g, 1.99 mmol),The reaction was carried out for 6 hours at room temperature. The reaction was quenched by adding water (10 mL) at 0 C.Extracted with ethyl acetate (20 mL×3).The combined organic phases were washed with a saturated sodium chloride solution (10 mL) and dried over anhydrous sodium sulfate, concentrated by suction filtration, and the residue was subjected to silica gel column chromatography[ethyl acetate / petroleum ether (v / v) = 1 / 9] purified,The title compound was obtained (0.40 g, yield 76%).It is a white solid.

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Li Jianhao; Gu Zheng; Deng Xinshan; Tang Wanjun; Zhang Zongyuan; Kang Panpan; Yuan Weihui; Peng Fei; (49 pag.)CN109942583; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5932-34-3, 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. 5932-34-3, name is Ethyl 4-bromo-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a microwave vial was added isopropyl alcohol (10 mL), ethyl 4-bromo-1H-pyrazole-3-carboxylate (from ChemBridge) (788 mg, 3.60 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (48.9 muL, 0.327 mmol) and 4-[3-(cyanomethylene)azetidin-1-yl]-2,5-difluoro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]benzamide (from Example 4 step 4, 1.13 g, 3.27 mmol). The reaction mixture was stirred at 80 C. for 2 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was purified with flash chromatography (eluting with 0-35% ethyl acetate in hexanes) to give the desired product as white foam. 1H NMR (500 MHz, DMSO) delta 8.61 (s, 1H), 8.47 (d, J=8.7 Hz, 1H), 7.34 (dd, J=12.5 and 6.3 Hz, 1H), 6.62 (dd, J=11.9 and 7.3 Hz, 1H), 4.76 (dt, J=15.5 and 7.8 Hz, 1H), 4.61 (d, J=9.2 Hz, 2H), 4.39 (d, J=8.0 Hz, 2H), 4.32 (q, J=7.1 Hz, 2H), 3.68 (s, 2H), 1.31 (m, 6H) ppm. LCMS calculated for C21H20BrF5N5O3 (M+H)+: m/z=564.1. Found: 563.8.

The synthetic route of Ethyl 4-bromo-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhuo, Jincong; Qian, Ding-Quan; Mei, Song; Cao, Ganfeng; Pan, Yongchun; Li, Qun; Jia, Zhongjiang; US2014/343030; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 39806-90-1, The chemical industry reduces the impact on the environment during synthesis 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-iodo-1-methyl-1H-pyrazole (55 gm, 0.264 moles) in N,N-dimethylacetamide (100 ml) was added 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). The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 90-110 C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30 C., to this added DI water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 min 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 60-70 C. The mixture was degassed for 2 hour at reduced pressure at 60-70 C., cooled the mixture to 20-30 C. Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30 C. The solid product obtained was filtered off, washed with cold DI water (100 ml) and dried at 40-50 C. to yield the product, 1-methyl-1H-pyrazole-4-carbonitrile.

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; Pawar, Jivan Dhanraj; Palimkar, Sanjay Sambhajirao; Sankar, B.; Kadam, Subhash Rajaram; Hindupur, Rama Mohan; Prabhu, Venkatesh M.; Pati, Hari Narayan; Suphala, Vadiraj Gopinath; Mane, Avinash Sheshrao; US2015/112063; (2015); 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., Formula: C13H20N4O4

Synthesis of compound 11b Compound 9b (200 mg, 0.67 mmol), and DIPEA (103 mg, 0.8 mmol) were dissolved in dichloromethane (25 ml), and cool down with ice water; 4-(chloromethyl)benzoyl chloride (compound 10b: 151 mg, 0.8 mmol) was dissolved in dichloromethane (25 ml), add drops at 0-5 C to the reaction solution, rise to the room temperature, and stir for 16 hours, vacuum evaporate the reaction solution and dissolve the residue with ethyl acetate, and wash the organic phase with water, dry the organic phase with sodium sulfate, evaporate the solvent with lower pressure, purify the residue with silica gel layer chromatography (ethyl acetate: petroleum ester=1:2), to give the yellow solid(compound 11b: 220 mg, 73% yield). 1H NMR (400 MHz, CD3OD) delta 7.98 (d, J=8.4 Hz, 2H). 7.60 (d, J=7.6 Hz, 2H). 4.74 (s, 2H), 4.69 (s, 4H), 4.50 (q, J=7.2 Hz, 2H), 1.55 (s, 9H), 1.45 (t, J=7.2 Hz, 3H).

The synthetic route of 398495-65-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu University; ZHENG, Zhebin; (36 pag.)EP3133069; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 138907-68-3, name is Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate, 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 138907-68-3, COA of Formula: C12H12FN3O2

PREPARATION G Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate A stirred suspension of ethyl 5-amino-1-(4-fluoro-phenyl)-1H-pyrazole-4-carboxylate (7.48 g, 30.0 mmole), prepared as described in Preparation A, above, and isopentyl nitrite (7.03 g, 60.0 mmole) in 80 ml of tetrahydrofuran was refluxed for twenty-four hours and then evaporated in vacuo. The residue was triturated with 50 ml of methanol and filtered to furnish 5.18 g (74% yield) of off-white solid. The sample was recrystallized from ethanol, m.p. 119-21 C. Analysis: Calculated for C12 H11 FN2 O2: C, 61.53; H, 4.73; N, 11.96%. Found: C, 61.41; H, 4.51; N, 11.95%.

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; Pfizer Inc.; US5064851; (1991); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics