Tag: M.W:100-200

Reference of 114474-28-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 114474-28-1 name is 4-(1H-Pyrazol-4-yl)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[0255] A mixture of 2,4-dichloropyrido[3,4-d]pyrimidine (250 mg, 1.25 mmol), 4-(lH- pyrazol-4-yl)aniline (199, 1.25 mmol), and iPr2NEt (0.44 mL, 2.50 mmol) in DMF (2.5 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (400 mg, 99%). MS (ES+) m/e 323 (M+H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1H-Pyrazol-4-yl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; KIM, Ji-In; POYUROVSKY, Masha; LIU, Kevin; BARSOTTI, Anthony; MORRIS, Koi; (344 pag.)WO2016/210330; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37622-90-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 37622-90-5 name is Ethyl 4-pyrazolecarboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Intermediate 8 -(4-Chloromethyl-benzyl)-1 H-pyrazole-4-carboxylic acid ethyl ester 1 H-Pyrazole-4-carboxylic acid ethyl ester (2 g, 13.9 mmol), (4-chloromethyl-phenyl)- methanol (2.21 g, 13.9 mmol) and triphenylphosphine (4.49 g, 16.8 mmol) are dissolved in tetrahydrofuran (40 ml). The solution is cooled to 0C then diethylazodicarboxylate(6.47 ml, 16.6 mmol) is added. The mixture is stirred at 0C for 2 hours, then 1 hour at room temperature. The solvent is removed under vacuum and the residue is purified by flash chromatography (0 – 50% ethyl acetate in cyclohexane) to give the title compound (Yield 1 .72 g). LC (Method 2): tR = 4.40 min; Mass spectrum (ES+): m/z = 279 [M+H ]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-pyrazolecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FRATTINI, Sara; BAKKER, Remko; GIOVANNINI, Riccardo; HAMPRECHT, Dieter; LINGARD, Iain; PAUTSCH, Alexander; WELLENZOHN, Bernd; (92 pag.)WO2017/72020; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 4149-06-8,Some common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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 mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

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

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 876343-24-7, The chemical industry reduces the impact on the environment during synthesis 876343-24-7, name is 1-Ethyl-1H-pyrazol-4-amine, I believe this compound will play a more active role in future production and life.

Example 1; iV-(l-ethyl-lJ-pyrazol-4-yl)-2-[2-methoxy-4-(l,6-naphthyridin-4-yloxy)phenyl]acetamide; Diisopropylethylamine (0.417 ml) and 2-(7-azabenzotriazol-l-yl)- 1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.395 g) were added in turn to a stirred mixture of 2-[2-methoxy-4-(l,6-naphthyridin-4-yloxy)phenyl]acetic acid (0.27 g),4-amino-l -ethyl- 1/i-pyrazole (0.179 g) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The resultant mixture was evaporated and the residue was purified by reversed-phase preparative HPLC on a Waters ‘Xbridge’ Cl 8 column (5 microns silica, 19 mm diameter, 100 mm length) using a solvent gradient comprising 13:17 to 100:0 mixtures of acetonitrile and 0.02M aqueous ammonium carbonate as eluent for 4.5 minutes at a flow rate of 40 ml per minute. The material so obtained was further purified by column chromatography on silica using a solvent gradient from methylene chloride to a 9:1 mixture of methylene chloride and 7M methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.12 g); 1H NMR Spectrum: (DMSOd6) 1.33 (t, 3H), 3.61 (s, 2H), 3.77 (s, 3H), 4.07 (q, 2H), 6.75 (d, IH), 6.91 (m, IH), 7.06 (d, IH), 7.37 (d, IH), 7.42 (s, IH), 7.88 (s, IH), 7.92 (d, IH), 8.82 (d, IH), 8.9 (d, IH), 9.71 (s, IH), 10.05 (s, IH); Mass Spectrum: M+H+404.

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-Ethyl-1H-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 2075-45-8 as follows. Formula: C3H3BrN2

Step 1 : 4-(Methylthio)-1H-pyrazole A suspension of 4-bromopyrazole (4 g, 27 mmol) in tetrahydrofuran (68 mL) was cooled to 0C and n-butyllithium (2.5 M in hexanes, 35.9 mL, 90 mmol) was added dropwise over a period of 20 min. The reaction mixture was stirred at room temperature for 1 h and then was cooled to 0C. 1 ,2-Dimethyldisulfide (2.66 mL, 30.0 mmol) was added dropwise. The reaction mixture was stirred at 0C for 1.5 h. The reaction mixture was poured into water (150 mL) and then it was acidified to pH~8 with a saturated aqueous solution of ammonium chloride and a solution of aqueous hydrochloric acid (1 N). The mixture was extracted with ethyl acetate (150 mL x 3) and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 4-(methylthio)-1 H-pyrazole (3300 mg). 1H NMR (500 MHz, CDCI3) delta 2.36 (s, 3H), 7.63 (s, 2H).

According to the analysis of related databases, 2075-45-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; AHN, Kay; BOEHM, Markus; CABRAL, Shawn; CARPINO, Philip A.; FUTATSUGI, Kentaro; HEPWORTH, David; KUNG, Daniel W.; ORR, Suvi; WANG, Jian; WO2013/150416; (2013); 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. 16034-48-3, name is 1-Pyrazoleacetic Acid, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O2

70 mg (0.19 mmol) of 3-amino-4-(cyclopropyloxy)-N-[6-(2-fluorophenyl)pyridin-3-yl]benzamide (intermediate 116), 29.2 mg (0.23 mmol) of IH-pyrazol-l-ylacetic acid, 130.3 mg (0.25 mmol) of PYBOP and 101 mu (0.58 mmol) of N-ethyl-N-isopropylpropan-2-amine in 3.5 mL of anh DMF were stirred for 5 h at 50 C. The reaction mixture was concentrated and purified by HPLC (Waters Autopurificationsystem SQD; column: YMC-Triart C18 5mu 100x30mm; eluent A: water + 0.1% vol. formic acid (99%), eluent B: acetonitrile; gradient: 0-0.50 min 24% B, 25 mL/min; 0.51-5.5 min 48- 66% B, 70 mL/min; temperature: room temperature) to yield 33 mg (36%) of the title compound. 1H-NM (300 MHz, DMSO-d6): delta [ppm]= 0.70 – 0.78 (m, 2H), 0.83 – 0.91 (m, 2H), 4.01 – 4.09 (m, IH), 5.13 (s, 2H), 6.33 (t, IH), 7.27 – 7.37 (m, 2H), 7.41 – 7.50 (m, 2H), 7.55 (d, IH), 7.76 – 7.86 (m, 3H), 7.90 – 7.99 (m, IH), 8.25 – 8.31 (m, IH), 8.62 (d, IH), 9.03 (d, IH), 9.26 (s, IH), 10.48 (s, IH). LC-MS (Method 3): Rt = 1.20 min; MS (ESIpos): m/z = 472 [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; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William J.; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; WO2014/147021; (2014); 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. 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H3F3N2

To a solution of 2-fluoro-3-hydroxybenzonitrile (0.92 g, 6.7 mmol) and4-(trifluoromethyl)-JH-pyrazole (1.0 g, 7.3 mmol) dissolved in 14 mL ofN,N-dimethylacetamide under a nitrogen atmosphere was added powdered potassium carbonate (2.78 g, 20.1 mmol). The resulting mixture was then heated at 153 C for 18 h. The cooled reaction mixture was diluted with de-ionized water and ethyl acetate and the layers separated. The aqueous layer was extracted (4X) with ethyl acetate, and the combined organic layers were washed (3X) with de-ionized water followed by brine. The combinedorganic layers were dried over Mg504, filtered and concentrated to give 1.58 g of an oil. Chromatography through 40 g of silica gel eluting with a gradient of 20 to 40% ethyl acetate in hexanes to give 1.37 g of a solid. The solid was filtered from hexanes to give 680 mg of the title compound.1H NMR oe 9.86 (bs, 1H), 8.64 (s, 1H), 8.07 (s, 1H), 7.40 (m, 2H), 7.37 (m, 1H).

According to the analysis of related databases, 52222-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; SHARPE, Paula Louise; STEVENSON, Thomas Martin; DEPREZ, Nicholas Ryan; REDDY, Ravisekhara P.; CHITTABOINA, Srinivas; WO2015/89003; (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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

To a solution of 10b (578.8 g, 4.13 mol) in DMAC (2.0 L) at 0 C was added thionyl chloride (514.7 g, 4.33 mol) dropwise, maintaining the temperature below 15 C. After addition of DMAC (0.25 L), the mixture was stirred at 0-15 C for 0.5 h. To this mixture was added 8 (500.0 g, 3.93 mol) portionwise, maintaining the temperature below 40 C. After addition of DMAC (0.75 L), the mixture was stirred at 15-40 C for 1 h. Then, H2O (1.0 L), NaOH (346.1 g, 8.65 mol) in H2O (4.5 L), and H2O (3.5 L) were successively added dropwise at 15-40 C. The resulting slurry was stirred for 2 h, and then filtered. Wet solids were washed with H2O (1.5 L) and dried in vacuo at 50 C to give the title compound 13b (923 g, 94%) as a pale brown solid; mp 188-189 C; 1H NMR (500 MHz, DMSO-d6) delta 2.19 (s, 3H), 3.98 (s, 3H), 6.62 (ddd, 4JHF=3.3 Hz, J=8.5, 3.3 Hz, 1H), 6.83 (s, 1H), 7.02 (dd, 4JHF=6.5 Hz, J=3.0 Hz, 1H), 7.07 (dd, 3JHF=10.0 Hz, J=9.0 Hz, 1H), 9.48 (br s, 1H), 9.85 (s, 1H); 13C NMR (125 MHz, DMSO-d6) delta 13.0, 38.5, 107.5, 112.9, 112.9, 115.8 (2JCF=21.3 Hz), 125.0 (2JCF=12.5 Hz), 135.2, 145.4, 149.0 (1JCF=235.0 Hz), 153.3 (3JCF=1.3 Hz), 158.0; IR (ATR) 3229, 1651, 1625, 1547, 1531, 1504, 1452, 1377, 1303, 1274, 1260, 1226, 1178, 1109, 1056, 1024, 973, 893, 850, 817, 804, 788, 771, 746, 678, 638, 624, 595, 527, 510, 461, 451, 432, 422, 412 cm-1; Anal. Calcd for C12H12N3O2F: C, 57.83; H, 4.85; N, 16.86. Found: C, 57.62; H, 4.69; N, 16.88.

The synthetic route of 78703-53-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishimoto, Kazuhisa; Sawai, Yasuhiro; Fukuda, Naohiro; Nagata, Toshiaki; Ikemoto, Tomomi; Tetrahedron; vol. 69; 40; (2013); p. 8564 – 8571;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H7BrN2

The title compound was obtained in analogy to example 48, intermediate a, from tert-butyl 4- oxo- 1 -phenyl- 1,3 ,8-triazaspiro [4. 5]decane-8-carboxylate (example 35, intermediate c) and 3- bromo-1,5-dimethyl-1H-pyrazole (CAS RN 5744-80-9) at 120C over 19 hours as a colorlesssolid. MS (ESI): mlz = 426.25 [M+H]; To a suspension of tert-butyl 4-oxo- 1 -phenyl- 1,3, 8-triazaspiro [4.51 decane- 8-carboxylate (100 mg, 302 imol, example 35, intermediate c) and 1-ethyl-3-iodo-1H-pyrazole (67 mg, 302 imol, CAS RN 120278 1-34-7) in dioxane (2 mL) were added K2C03 (125 mg, 905 imol), DMEDA(6.11 iL, 48.3 imol, CAS RN 110-70-3) and Cul (4.6 mg, 24.1 imol) and the mixture was purged with argon. The suspension was heated to 100C and stuffed at this temperature over 14 hours. The reaction mixture was filtered over a microfilter, the filtrate was washed with a small volume of EtOAc and MeOH, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 4 g column using an MPLC (ISCO) system elutingwith a gradient of n-heptane : EtOAc (100: 0 to 50: 50) to give the title compound as a colorless solid (0.107 g; 83.3%).

The synthetic route of 5744-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; RUDOLPH, Markus; SATZ, Alexander Lee; (204 pag.)WO2017/5583; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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 4149-06-8, Application In Synthesis of 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics