Tag: M.W=300-400

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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

Synthesis of N-Boc-N’-n-octyl-1-guanylpyrazole Under ice-cooling and under nitrogen atmosphere, to a suspension of NaH (60% in oil, 283 mg, 7.08 mmol) in DMF (10 mL)) was added N,N’-bis-Boc-1-guanylpyrazole (2 g, 6.44 mmol) by small portions. After stirring at the same temperature for 15 min, 1-iodooctane (2.33 mL, 12.9 mmol) was added dropwise, and the mixture was stirred overnight while raising the temperature to room temperature. Under ice-cooling, water was added to discontinue the reaction, and the whole mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl solution, and dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography using n-hexane:AcOEt=8:1 as an eluate to give the object product as an oil (yield: 1.8 g, 66.1%). 1H NMR (300 MHz, CHLOROFORM-d) deltappm 0.78-0.92 (3H, m), 1.19-1.36 (10H, m), 1.27 (9H, s), 1.50 (9H, s), 1.65-1.81 (2H, m), 3.61-3.69 (2H, m), 6.41 (1H, dd, J=2.7, 1.6 Hz), 7.69 (1H, d, J=1.1 Hz), 7.93 (1H, br. s.)

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2012/172293; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 152120-54-2, 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 152120-54-2 as follows.

Compound 6 (1.47 kg) is dissolved in methanol (11.6 kg), then 10% Pd-C (143 g) is added under nitrogen atmosphere. The resulting reaction mixture is stirred 2.5 hours under hydrogen at ambient pressure, and then catalyst is removed by filtration. To the filtrate, 1N HCl (2 L), triethylamine (420 g) and di-boc-guanylpyrazole (0.70 g) are added in order. The resulting reaction mixture is stirred at room temperature for 102 minutes. Then it is evaporated, followed by dilution with ethyl acetate (10.7 kg). The organic layer washed with sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The crude compound 8 is purified by column chromatography with 1.9 kg of silica gel and ethyl acetate/ dichloromethane to methanol/dichloromethane. Yield: 1.19 kg (62.3%), expected HPLC purity: about 96.4%

According to the analysis of related databases, 152120-54-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLCEUTIX CORPORATION; MENON, Krishna; (75 pag.)WO2016/133733; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 152120-54-2, These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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: N,N-diBoc-1H-pirazole-1-carboxamidine (0.8 g, 1eq) was dissolved in anhydrous THF (10 mL), then triphenylphosphine (1.01 g, 1.5eq) and the appropriate alcohol (1.3 eq) were. The mixture was then cooled to 0 C and DIAD (0.76 mL, 1.5eq) was added dropwise. The temperature was raised to reflux and stirred overnight. The reaction was quenched with H2O and extracted with CH2Cl2 (3 x 30 mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified by flash column chromatography (SiO2) using 1:9 AcOEt / Petroleum ether as the eluent to yield the guanilated agent.

Statistics shows that tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate is playing an increasingly important role. we look forward to future research findings about 152120-54-2.

Reference:
Article; Maccari, Giorgio; Sanfilippo, Stefania; De Luca, Filomena; Deodato, Davide; Casian, Alexandru; Dasso Lang, Maria Chiara; Zamperini, Claudio; Dreassi, Elena; Rossolini, Gian Maria; Docquier, Jean-Denis; Botta, Maurizio; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5525 – 5529;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 120068-79-3,Some common heterocyclic compound, 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, molecular formula is C11H5Cl2F3N4, 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 1; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with triethylamine hydrochloride, sodium trifluoromethylsulfinate and thionylchloride, in 6.5 molar equivalents of tolueneWithin a 3-neck, 50 ml. round bottom flask equipped with a magnetic stirrer bar and a thermometer were placed vacuum dried sodium trifluoromethylsulfinate (4.29 g, 27.5 mmol), vacuum dried triethylamine hydrochloride (5.16 g, 37.5 mmol), and 13 ml. an- hydrous toluene (6.5 molar equivalents relative to 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H-pyrazole-3-carbonitrile) under an argon atmosphere. After cooling to 00C to 5 0C with an ice bath, thionylchloride (3.57 g, 30 mmol) was added slowly while keeping the reaction temperature below 5 0C. After stirring for another 30 min, vacuum dried 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-1 H-pyrazole-3- carbonitrile (8.03 g, 25 mmol, 99 % purity) was added at 5 0C, and the reaction mixture was heated to 50 0C within 5 min by a preheated water bath. The temperature of 50 0C was kept for another 6 hours before quenching the reaction with 50 ml. of saturated NaHCO3 solution. The resulting suspension was diluted with 30 ml. of ethylacetate. After phase separa- tion the organic layer was washed once with saturated NaHCtheta3 solution and concentrated under reduced pressure until dryness. The crude product was crystallized from refluxing toluene (100 g) affording the title compound as a white crystalline powder (8.06 g, 70 % yield, 94 % purity by quantitative HPLC). 1H-NMR (Bruker DRX-500, d6- DMSO): delta [ppm]: 8.33 (s), 7.57 (s).; Comparative Examples; In order to demonstrate the advantages of the inventive process, the following examples are conducted employing the preparation procedure given above for example 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, its application will become more common.

Reference:
Patent; BASF SE; WO2008/55877; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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 152120-54-2, Safety of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

To a solution of 2-(benzyloxycarbonylamino)ethoxyamine (780 mg, 3.7 mmol), as prepared in the preceding step, in N,N-dimethylformamide (20 mL) was added [N,N’-di(tert-butoxycarbonyl)]amidinopyrazole (1.25 g, 4.0 mmol). The mixture was stirred at room temperature overnight, and the solvent evaporated under high vacuum. The residue was purified by flash column chromatography (0-5% ethyl acetate in methylene chloride) to give the title compound as a colorless oil (1.55 g, 93%). 1H-NMR (300 MHz, CDCl3) delta 9.08 (s, 1H), 7.67 (s, 1H), 7.33 (m, 5H), 6.21 (br s, 1H), 5.21 (br s, 1H), 5.11 (s, 2H), 4.12 (t, J=4.8 Hz, 2H), 3.54 (q, J=4.9 Hz, 2H), 1.49 (s, 9H), 1.46 (s, 9H).

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; Kreutter, Kevin D.; Lee, Lily; Lu, Tianbao; Mohan, Venkatraman; Patel, Sharmila; Huang, Hui; Xu, Guozhang; Fitzgerald, Mark; US2004/254166; (2004); 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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

General procedure: Diisopropyl azodicarboxylate (DIAD, 1.5 equiv) was added dropwise to a stirred solution of alcohol 1a-g (1-2 equiv), N,N?-bis-tert-butoxycarbonylpyrazole-1H-carboxamidine 2 (2.5 mmol, 1 equiv), and Ph3P (1.5 equiv) in THF (7 mL) at 0 C. The reaction mixture was stirred overnight (16 h) at r.t., concentrated in vacuum, and the residue was purified by flash column chromatography on silica gel (10-25% EtOAc-hexane) to give the N-alkylated guanylating agent 3a-g as colorless oils.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 152120-54-2.

Reference:
Article; Tommasi, Sara; Zanato, Chiara; Carabeo, Rey; Mangoni, Arduino A.; Dall’Angelo, Sergio; Zanda, Matteo; Synthesis; vol. 47; 19; (2015); p. 3067 – 3078;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 120068-79-3,Some common heterocyclic compound, 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, molecular formula is C11H5Cl2F3N4, 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: A mixture of compound A (5 mmol) and corresponding benzaldehyde (5 mmol) in 10 mL ethanol was refluxed for 24 hours in a reaction flask wrapped up by silver paper. Upon the reactions completed (monitored by TLC), tawny solids were obtained through suction filtration. The precipitates were washed with ethanol (5 mLx3) and recrystallized from ethanol with 50-84% yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, its application will become more common.

Reference:
Letter; Li, Guanglong; Zhou, Cong; Zhu, Chengchun; He, Lujue; Li, Xiaoyang; Xu, Zhiping; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong; Cheng, Jiagao; Letters in drug design and discovery; vol. 16; 10; (2019); p. 1175 – 1180;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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 152120-54-2, Recommanded Product: tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

To a mixture of N,N’-bis(tertbutoxycarbonyl)-1H-pyrazole-1-carboxamidine (2g, 6.44 mmol), triphenylphosphine (2.53g, 9.67 mmol), MeOH (260 muL, 6.44 mmol) and dry THF (20 mL) was added dropwise DIAD ( 1.9 mL, 9.67 mmol) at 0C under argon. The reaction mixture was stirred at room temperature overnight. Then a solid was filtered off and the filtratrate was concentrated under reduced pressure. A residue was washed with hexane (6 x 50mL). Hexane was evaporated and the residue was purified by column chromatography on silica gel (hexane/AcOEt, 7: 1 to 5: 1) to give tert-butyl (((tert-butoxycarbonyl)imino)(1H-pyrazol-1-yl)methyl)(methyl)carbamate (1.49 g, 71 %) as a colorless oil . ESI+MS: m/z = 347.1 (M+1)+. 1Eta NMR (700 MHz, Chloroform-d) delta 8.02 (s, 1H), 7.71 (d, J= 1.1 Hz, 1H), 6.45 (ddd, J = 8.7, 2.7, 1.6 Hz, 1H), 3.27 (s, 3H), 1.54 (s, 9H), 1.32 (s, 9H).

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, tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ONCOARENDI THERAPEUTICS SP. Z O.O.; B?ASZCZYK, Roman; BRZEZI?SKA, Joanna; GO??BIOWSKI, Adam A.; OLCZAK, Jacek; (93 pag.)WO2016/108707; (2016); 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 120068-79-3 as follows. name: 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

General procedure: A mixture of compound A (5 mmol) and corresponding benzaldehyde (5 mmol) in 10 mL ethanol was refluxed for 24 hours in a reaction flask wrapped up by silver paper. Upon the reactions completed (monitored by TLC), tawny solids were obtained through suction filtration. The precipitates were washed with ethanol (5 mLx3) and recrystallized from ethanol with 50-84% yields.

According to the analysis of related databases, 120068-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Letter; Li, Guanglong; Zhou, Cong; Zhu, Chengchun; He, Lujue; Li, Xiaoyang; Xu, Zhiping; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong; Cheng, Jiagao; Letters in drug design and discovery; vol. 16; 10; (2019); p. 1175 – 1180;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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. category: pyrazoles-derivatives

General procedure: To a stirred solution of N,N?-Di-Boc-1H-pyrazole-1-carboxamidine (1.61 mmol) in dry THF, Ph3P(1.42 mmol) and the appropriate alcohol (2.10 mmol) were added under N2 atmosphere. The solutionwas cooled at 0 C and DIAD (2.42 mmol) was added dropwise. The reaction mixture was stirred atreflux for 16 h. The solvent was evaporated and DCM and water were added. Organic phase wasseparated and the aqueous layer was extracted with DCM. The residue was purified by flashchromatography (Hexane/AcOEt 9:1) affording desired compound.

The synthetic route of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maccari, Giorgio; Deodato, Davide; Fiorucci, Diego; Orofino, Francesco; Truglio, Giuseppina I.; Pasero, Carolina; Martini, Riccardo; De Luca, Filomena; Docquier, Jean-Denis; Botta, Maurizio; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3332 – 3336;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics