Tag: M.W:200-300

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. 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 51516-67-7

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.

The synthetic route of 51516-67-7 has been constantly updated, and we look forward to future research findings.

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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Some common heterocyclic compound, 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, molecular formula is C7H7F3N2O2, 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. HPLC of Formula: C7H7F3N2O2

To a solution of 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetic acid (2.75 g, 0.013 mol) in N, N-dimethylforamide (22 ml), 1-[bis(dimethylamino)methylene]-1 H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (5.27 g, 0.014 mol), 3-methylsulfanylpiperidine- 4-carbonitrile hydrochloride (2.55 g, 0.013 mol) and triethylamine (5.52 ml, 0.04 mol) at 0C was added and allowed to stirred at room temperature for 3 hrs. After completion of reaction, the reaction mixture was diluted with water extracted with ethyl acetate. The organic layerwas washed with water, brine and dried over sodium sulphate. Organic layer was concentrated to dryness. The residue was washed with diethyl ether afforded 3.5 g of 3-methylsulfanyl-1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]pi peridine-4-carbonitrile.MS: m/z = 347 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 345637-71-0, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; LAMBERTH, Clemens; SULZER-MOSSE, Sarah; CEDERBAUM, Fredrik; UMARYE, Jayant; SONAWANE, Ravindra; WO2013/127808; (2013); A1;,
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1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, 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. Computed Properties of C10H15N3O2

INTERMEDIATE 4; Step A: fert-Butyl 2-(2-aniino-2-oxoemyl)-2,6-dihvdropvrrolof3,4-c|pyrazole-5(4H)- carboxylateA 2 L three neck flask fitted with a thermometer, a mechanical stirrer and an addition funnel was charged with a suspension of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole- 5(4H)-carboxylate (18.01 g, 86.5 mmol) in anhydrous acetonitrile (1.0 L). Sodium hydride (60% dispersion in oil, 4.15 g, 104 mmol) was added to the suspension in one portion under nitrogen. The reaction was stirred at room temperature for 2 h. The resulting white suspension was then cooled in an ice bath and iodoacetamide (31.95 g, 173 mmol) was added. The ice bath was then removed and the mixture was stirred 18 h at room temperature. The mixture was quenched with water (50 mL) and the solvent was removed under reduced pressure. The residue was partitioned between diluted NaCl (50 mL brine and 100 mL water) and 1.0 L EtOAc. The aqueous layer was extracted with 2 1.0L EtOAc. The organic layers were combined and dried over Na2S04 and solvent was evaporated under reduced pressure. Crude material was purified on silica gel eluting with 20-50%EtOAc/CH2Cl2 to wash out excess iodoacetamide, and then with 2- 10%MeOH CH2Cl2 to afford a mixture of the two products which were separated on a chiral AD column by eluting with 30% MeOH/C02 to afford the title compound (less mobile fraction). LC- MS – 267.32 [M+l].

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WILKENING, Robert, R.; APGAR, James, M.; BIFTU, Tesfaye; FENG, Danqing; QIAN, Xiaoxia; WEI, Lan; WO2011/103256; (2011); A1;,
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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 1280210-79-8 as follows. Formula: C10H15N3O2

Step 2. A solution of tert-butyl 2H,4H,5H,6H-pyrrolo[3,4-c]pyrazole-5- carboxylate (250 mg, 1 . 1 mmol, 1 ,00 equiv) in DCM (5 mL) and TFA (5 mL) was stirred at rt overnight. The reaction mixture was concentrated under vacuum and the residue was redissolved in 20 mL of concentrated HC1 and then concentrated under vacuum again to yield 200 mg of crude 2H,4H,5H,6H-pyrrolo[3 ,4-c]pyrazole hydroch loride as a dark red sol id. LC/MS ( Method C, ESI): RT = 0.46 min, m z = 1 1 0.0 [M+H] .

According to the analysis of related databases, 1280210-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; DRAGOVICH, Peter; GOSSELIN, Francis; YUEN, Po-Wai; ZAK, Mark; ZHENG, Xiaozhang; WO2013/127267; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, 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 37687-24-4, COA of Formula: C9H12N2O4

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (2.00 g, 9.42 mmol), 2-bromo-1-(3,4-dihydro-2/-/-chromen-2-yl)ethanone (Intermediate 209A, 2.52 g, 9.90 mmol) and potassium carbonate (1.43 g, 10.4 mmol) in dry acetone (50 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 concen- trated. The residue was purified by flash-chromatography on silica gel (80 g, eluent: 0-25% ethyl acetate in petroleum ether) to give the title compound (2.88 g, 79% of theory). 1H-NMR (300 MHz, CDCIs): d [ppm] = 7.44 (s, 1H), 7.21-7.16 (m, 1H), 7.12-7.10 (m, 1H), 6.95- 6.90 (m, 2H), 5.95 (d, 1H), 5.69 (d, 1H), 4.75-4.71 (m, 1H), 4.42 (q, 2H), 4.30 (q, 2H), 2.88-2.82 (m, 2H), 2.36-2.17 (m, 2H), 1.40 (t, 3H), 1.35 (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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Application of 51516-67-7, 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. 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Intermediate 4 (1mmol) and the intermediate 7 (1mmol) were dissolved in ethanol to the glass flask, then HCl solution was added as a catalyst refluxed at 80C for 15-18h. After the TLC monitoring reaction was completed, the mixture was vacuum filtered and concentrated. Finally, the above crude product can be isolated and purified by column chromatography (Hexane/EtOAc=8:1) to obtain target compounds.

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, 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cao, Hai-Qun; Chu, Zhi-Wen; Liu, Hao; Lv, Xian-Hai; Xia, Dong-Guo; Bioorganic Chemistry; vol. 99; (2020);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 277299-70-4,Some common heterocyclic compound, 277299-70-4, name is 2-(3,4-Dimethylphenyl)-5-methyl-1H-pyrazol-3(2H)-one, molecular formula is C12H14N2O, 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.

b 4-{[1-(3,4-Dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl]azo}-3-hydroxybenzoic Acid Following the procedure of Example 1, except substituting 1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one for 3-methyl-1-(4-methylphenyl)-3-pyrazolin-5-one, the title compound was prepared as an orange solid (1.5 g, 82%). 1H NMR (400 MHz, d6-DMSO) delta 13.5 br s, 1H), 11.0 (s, 1H), 7.70 (m, 2H), 7.61 (dd, J=8.2 and 2.1 Hz, 1H), 7.53 (m, 2), 8.20 (d, J=8.2 Hz, 1H), 2.30 (s, 3H), 2.27 (s, 3H), 2.22 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,4-Dimethylphenyl)-5-methyl-1H-pyrazol-3(2H)-one, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6642265; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

330792-70-6, name is 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, 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. Safety of 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile

[0383] A mixture of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (1.0 g, 3.6mmol), ethyl2-(l-benzylpiperidin-4-ylidene)acetate (1.1 g, 4.3 mmol) and K2C03 (745 mg, 5.4mmol) in DMF (20 mL) was heated to 80 °C for 16 hr under N2? The reaction was quenchedwith water (20 mL) and extracted with EA (20 mL x 3). The combined organic layers were driedover Na2S04, concentrated and purified by chromatography column on silica gel using 30percent ofEA in PEas eluant to give the product (950 mg, 54.9percent) as a yellow solid. 1H NMR (400 MHz,DMSO-d6) 8 11.92 (s, 1H), 7.84 (d, J = 8.8 Hz, 2H), 7.48-7.40 (m, 2H), 7.36-7.29 (m, 4H), 7.27-7.23 (m, 1H), 7.20 (t, J = 7.6 Hz, 1H), 7.15-7.07 (m, 4H), 3.55 (s, 2H), 3.01 (s, 2H), 2.81-2.73(m, 2H), 2.39-2.27 (m, 2H), 2.26-2.16 (m, 2H), 1.83-1.74 (m, 2H). MS (ESI, m/e) [M+1t 489.9.

The synthetic route of 330792-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUO, Yunhang; BEIGENE, LTD.; WANG, Zhiwei; WO2014/173289; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 13599-12-7, 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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture of 5 (105 g, 573 mmol), K2CO3 (119 g, 860 mmol), and DMF (400 mL) was added benzyl bromide (117 g, 687 mmol). After being stirred at room temperature for 15 h, the mixture was poured into water and extracted with EtOAc. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/EtOAc, 100:1 to 4:1) to give 6 (130 g, 83%) as a pale yellow oil.

The synthetic route of Ethyl 3-phenyl-1H-pyrazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rikimaru, Kentaro; Wakabayashi, Takeshi; Abe, Hidenori; Imoto, Hiroshi; Maekawa, Tsuyoshi; Ujikawa, Osamu; Murase, Katsuhito; Matsuo, Takanori; Matsumoto, Mitsuharu; Nomura, Chisako; Tsuge, Hiroko; Arimura, Naoto; Kawakami, Kazutoshi; Sakamoto, Junichi; Funami, Miyuki; Mol, Clifford D.; Snell, Gyorgy P.; Bragstad, Kenneth A.; Sang, Bi-Ching; Dougan, Douglas R.; Tanaka, Toshimasa; Katayama, Nozomi; Horiguchi, Yoshiaki; Momose, Yu; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 714 – 733;,
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Pyrazoles – an overview | ScienceDirect Topics

Reference of 5932-30-9, These common heterocyclic compound, 5932-30-9, name is Ethyl 5-phenyl-1H-pyrazole-3-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.

The starting material (100 mg, 0.46 mmol) was dissolved in 10 mL of acetone.Add potassium carbonate (190 mg, 1.38 mmol) and potassium iodide (8 mg, 0.046 mmol),Dimethyl sulfate (31.5 mg, 0.25 mmol), refluxing for 4 h,After TLC detects the reaction, it is filtered.The filter cake was washed with 10 mL of ethyl acetate and 10 mL of dichloromethane until no fluorescence.The filtrates were combined and concentrated.Column chromatography purification (petroleum ether: ethyl acetate = 4:1)Yellow solid99mg,Yield 93.4%,

The synthetic route of 5932-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Wang Jinxin; Yang Kan; Zhi Zhuoer; Nong Keyi; (8 pag.)CN109232426; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics