Category: 28466-26-4

Related Products of 28466-26-4, A common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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.

To a solution of 4-Aminopyrazole (111 mg, 1.00 mmol) in DMF (3.3 mL) in a 20 mL vial was added 2,4-Dichloro-6-trifluoromethylquinazoline (200 mg, 1.00 mmol) and DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight, cooled to rt and poured into water. The precipitate that was formed was filtered and washed with water, dried on the filter for 1 h then in a desiccator overnight to give 227 mg of a grey solid that was used as is in the next step. MS (ES+) m/e 314/316 (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; KADMON CORPORATION, LLC; LIU, Kevin G.; OLSZEWSKI, Kellen L.; KIM, Ji-In; POYUROVSKY, Masha V.; MORRIS, Koi; YU, Xuemei; LAMARQUE, Christophe; (0 pag.)WO2020/5935; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, 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. 28466-26-4 name is 4-Aminopyrazole, 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.

Example 150 3-[(2-chlorophenoxy)methyl]-N-1H-pyrazol-4-ylbenzamide 3-[(2-Chlorophenoxy)methyl]benzoic acid was suspended in tetrahydrofuran (50 mL), and oxalyl chloride (1.03 mL) and N,N-dimethylformamide (catalytic amount) were added. After stirring at room temperature for 30 min, the mixture was added dropwise to a suspension of 1H-pyrazol-4-amine (1.0 g) in N,N-dimethylacetamide (50 mL). After stirring at room temperature for 5 hr, ethyl acetate was added, and the mixture was washed 3 times with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography and recrystallized from ethyl acetate/hexane to give the object product (280 mg, 7.8%). 1H NMR (300 MHz, DMSO-d6) delta ppm 5.29 (s, 2H) 6.93-7.02 (m, 1H) 7.22-7.35 (m, 2H) 7.46 (dd, J=1.51, 7.91 Hz, 1H) 7.56 (t, J=7.72 Hz, 1H) 7.63-7.70 (m, 1H) 7.85 (brs, 2H) 7.89-7.95 (m, 1H) 8.02-8.06 (m, 1H) 10.47 (s, 1H) 12.63 (brs, 1H)

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

Reference:
Patent; Taniguchi, Takahiko; Miyata, Kenichi; Kubo, Osamu; Matsui, Junji; US2009/325956; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 28466-26-4, name is 4-Aminopyrazole, 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 28466-26-4, Formula: C3H5N3

Step 2: To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (1 1.18 g) in DCM (65 mL), HOBT (1 1 .15 g, 0.083 mol) and EDC (15.8 g, 0.083 mol) was added at 0 C. This suspension was stirred at this temperature for 10 min, then it was added to a suspension was of 1 /-/-pyrazol-4-amine (5.48 g) and DIPEA (17.65 mL) in DCM (50 mL). The resulting mixture was allowed to warm to rt and was stirred at rt for 18 h. Percipitation of the desired compound was obtained by the addition of water. The solid was filtered and dried to yield the title compound. LC-MS conditions B: tR = 0.63 min, [M+H]+ = 269.13.

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; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); 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. 28466-26-4, name is 4-Aminopyrazole, A new synthetic method of this compound is introduced below., Formula: C3H5N3

3.0 g of 4-amino-1H-pyrazole (2) was dissolved in a 7.5 g / 160 mL NaHCO3 / tetrahydrofuran mixed solution, 8.6 g of di-tert-butyl dicarbonate was added and reacted at room temperature for 2 days. The solvent was evaporated to dryness on a rotary evaporator, and then dissolved with ethyl acetate, and washed three times with water, aqueous citric acid, and saturated sodium chloride solution; The organic phase was dried over anhydrous magnesium sulfate over night and filtered and evaporated After the crude product was washed with n-hexane, a pure 5.0 g of a pink solid 3 was obtained in a yield of 75%.

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; Shandong University; Zhang Yingjie; Liang Xuewu; Xu Wenfang; (47 pag.)CN108864057; (2018); A;,
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 28466-26-4 as follows. category: pyrazoles-derivatives

General procedure: 3 -Phenyl- lH-pyrazol-4-amine (100.0 mg, 0.6 mmol, 1.0 equiv) was dissolved in THF (15.0 mL). TEA (l27. l mg, 1.3 mmol, 2.0 equiv) and l-butyl-4-isocyanatobenzene (132.1 mg, 0.8 mmol, 1.2 equiv) were added dropwise. The solution was then stirred for 2 hours at RT. The resulting solution was concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions: Column: XBridge Prep OBD C18 Column, 30x l50mm 5um; Mobile Phase A:Water (10 MMOL/L NH4HCO3), Mobile Phase B:ACN; Flow rate:60 mL/min; Gradient:50% B to 82% B in 7.5 min; UV 254/210 nm; RTl :4.48. l-(4-Butylphenyl)-3-(3-phenyl-lH-pyrazol-4-yl)urea (30 mg, 14.3%) was isolated as a white solid. LCMS Method G, MS-ESI: 335. l[M+H+]

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IFM DUE, INC.; ROUSH, William R.; VENKATRAMAN, Shankar; GLICK, Gary; SEIDEL, Hans Martin; (171 pag.)WO2020/10155; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, 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 28466-26-4 as follows.

3-(2-(Methoxycarbonyl)phenyl)acrylic acid (1.23 g, 5.97 mmol) was weighed.EDCI (1g, 5.24mmol), DMAP (0.35 g, 2.87 mmol) was dissolved in THF (18 mL) and stirred at room temperature.Compound 1H-pyrazole-4-amine (0.56 g, 5.6 mmol) was then added.The system was stirred at room temperature overnight.Add water to filter the sediment,Concentration in vacuo gave a crude product (yield: 0.72 g, 2.66 mmol) as a white solid.

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing University of Technology; Zhang Na; Qi Xiaoqian; Li Chunqiong; Zhao Lijiao; Zhong Rugang; (8 pag.)CN109879808; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 28466-26-4, These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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.

Acetic anhydride (0.7 ml, 8.433 mmol) was added dropwise at 0 C. to 1H-pyrazol-4-amine (0.7 g, 8.433 mmol). The mixture was stirred for 30 min at RT and quenched by the addition of crushed ice. The mixture was extracted with ethyl acetate The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 54% yield. (0.6 g). LC-MS (ESI): Calculated mass: 125.0; Observed mass 126.0 [M+H]+ (rt: 0.115 min).

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (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. 28466-26-4, name is 4-Aminopyrazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Aminopyrazole

1/-/-Pyrazol-4-amine (for a preparation see intermediate 1 ; 0.54 g, 6.5 mmol) was dissolved in acetonitrile (25 ml) with triethylamine (1.81 ml, 13.0 mmol) to give a red- purple suspension which was cooled in an ice-water bath. To the suspension was added a solution of 2,6-difluorobenzoyl chloride (Aldrich; 0.817 ml, 6.5 mmol) in acetonitrile (25 ml) dropwise over 15 min. The mixture was stirred cold under nitrogen. The reaction was stirred and allowed to warm slowly towards room temperature over 2 h, then at room temperature for 30 min. The reaction mixture was partitioned between EtOAc and water (-100 ml each). The aqueous phase was extracted with further EtOAc (2 x 50 ml). The combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue (1.41 g) was purified on silica (50 g) using 0-100% EtOAc-cyclohexane then 0-20% methanol- EtOAc. Relevant fractions were concentrated in vacuo to give some pure product (0.925 g) and some less pure material (0.50 g). The latter material was re-purified on silica (20 g) using EtOAc to give further pure product (0.366 g). The two batches of pure product were combined to give the title compound (1.28 g) as a pale cream solid; LCMS (System 1): MH+= 224, tRET = 2.08 min.

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; GLAXO GROUP LIMITED; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; WO2012/52459; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, 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. 28466-26-4 name is 4-Aminopyrazole, 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.

[00606] Synthesis of compound 1-78. Compound 1-78 was prepared from compounds 3.4 and 96.2 using protocol described in Example 94. . LCMS (ES, m/z): 440 [M+H]+; 1H-NMR (300 MHz, DMSO) delta 8.87 (1H, s), 7.82 (1H, brs), 7.52 (1H, brs), 5.71 (1H, d), 4.05-3.89 (1H, m), 3.58 (4H, brs), 3.01-2.95 (2H, m), 2.84-2.79 (2H, m), 2.50 (4H, m), 2.42-2.34 (2H, m), 2.26- 2.18 (1H, m), 2.05 (2H, d), 1.92 (2H, d), 1.47-1.30 (4H, m). [00599] Example 94. Synthesis of 2-(4-((4-(((lr,4r)-4-morpholinocyclohexyl)amino)-6,7- dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-2-yl)amino)-lH-pyrazol-l-yl)acetate, Example 1-76 [00600] To a solution of intermediate 3.4 (50 mg, 0.13 mmol, 1.00 equiv) and 2-(4-amino- lH-pyrazol-l-yl)acetic acid (36 mg, 0.26 mmol, 2.00 equiv) in isopropanol (5 mL) was added hydrochloric acid (4 M in dioxane, 0.1 mL) at room temperature. The reaction was stirred for 2 h at 140 C and irradiated in microwave. The resulting mixture was concentrated under vacuum and resulting crude was purified to yield compound 1-76 as a yellow solid. LCMS (ES, m/z) 540 [M+H]+. 1H NMR (300 MHz, d6-OMSO, ppm): delta 8.99 (s, 1H), 7.90 (s, 1H), 7.51 (s, 1H), 7.26-7.06 (m, 1H), 5.79-5.71 (m, 1H), 4.99-4.91 (m, 3H), 4.01-3.99 (m, 1H), 3.77-51 (m, 4H), 3.05-2.98 (m, 2H), 2.83-2.73 (m, 2H), 2.61-2.53 (m, 5H), 2.40-2.35 (m, 2H), 2.01-1.94 (m, 2H), 1.49-1.35 (m, 4H), 1.20-1.15 (m, 6H).

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

Reference:
Patent; NIMBUS IRIS, INC.; CHAUDHARY, Divya; KAPELLER-LIBERMANN, Rosana; WO2014/194242; (2014); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 28466-26-4, name is 4-Aminopyrazole, 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 28466-26-4, COA of Formula: C3H5N3

General procedure: Different five-membered heterocyclic amines (1.72 mmol) and sodiumcarbonate (0.36 g, 3.44 mmol) were added to anhydrous tetrahydrofuran(10 mL) at 0 C. Then, 15b (0.35 g, 1.72 mmol) dissolved in5 mL of tetrahydrofuran was added. Stirring was continued for an additional1 h in the ice bath (monitored by TLC). The organic phase wasfiltered and the diethyl ether (10 mL) was added to the filtrate. Finally,the solid was precipitated from the filtrate to afford the intermediates16i-k. 4.1.6.1. 2-bromo-N-(1H-pyrazol-4-yl)acetamide (16i). The crude 16iwas used directly in the next step without further purification

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:
Review; Wang, Zhao; Yu, Zhao; Kang, Dongwei; Zhang, Jian; Tian, Ye; Daelemans, Dirk; De Clercq, Erik; Pannecouque, Christophe; Zhan, Peng; Liu, Xinyong; Bioorganic and Medicinal Chemistry; vol. 27; 3; (2019); p. 447 – 456;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics