Category: 152120-54-2

Synthetic Route 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: Method B. The required amine hydrochloride salt 7 (1.5-6.0 equiv) and pyrazole-1-carboxamide 6a (1.0 equiv) were dissolved in acetonitrile or chloroform (ca. 1 mL per mmol) and triethylamine (twofold excess based on 7) was added drop-wise with stirring, together with anhydrous MgSO4 to dryness. After 16 h the mixture was filtered, evaporated and purified by column chromatography on silica.

The synthetic route of 152120-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Al Shuhaib, Zainab; Davies, Deiniol H.; Dennis, Mark; Evans, Daniel M.; Fletcher, Matthew D.; Franken, Herjan; Hancock, Paul; Hollinshead, Jackie; Jones, Iestyn; Kaehm, Kristina; Murphy, Patrick J.; Nash, Robert; Potter, David; Rowles, Richard; Tetrahedron; vol. 70; 29; (2014); p. 4412 – 4419;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 152120-54-2, 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.

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.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate. I believe this compound will play a more active role in future production and life.

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

Related Products of 152120-54-2, A common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, molecular formula is C14H22N4O4, 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 N-alpha-Boc-D-lysine (13.0 g, 52.7 mmol) in EtOH (290 mL) was added N,N’-bis-Boc-1-guanylpyrazole (16.3 g, 52.7 mmol) and triethyl amine (10.6 g, 105 mmol). The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was purified by column chromatography (silica gel, 10:1 CH2Cl2/MeOH) to afford a pyrazole salt (25.0 g) as colorless oil. _The salt was dissolved in 1 N NaOH (300 mL) and neutralized with 1 N HCl (305 mL) The resulting precipitate was filtered out and dried, to afford compound 3 (22.0 g, 85%) as a white solid: 1H NMR (400 MHz, CDCl3) delta 11.48 (br s, 1H), 8.35 (br s, 1H), 5.23 (d, J=7.5 Hz, 1H), 4.23 (br s, 1H), 3.48-3.25 (m, 2H), 1.96-1.50 (m, 6H), 1.51 (s, 9H), 1.49 (s, 9H), 1.43 (s, 9H).

The synthetic route of 152120-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PARION SCIENCES, INC.; JOHNSON, Michael Ross; THELIN, William Robert; BOUCHER, Richard C.; US2013/324559; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 152120-54-2, 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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of piperidine-4-carboxylic acid trifluoroacetate salt (0.20 g, 0.82 mmol) in methanol (10 mL), triethylamine (0.20 mL, 1.6 mmol) and N,N’-bis{[(2-methyl-2-propanyl)oxy]carbonyl}-1H-pyrazole-1-carboximidamide (0.30 g, 0.98 mmol) was added and the reaction mixture stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure and the resulting residue dissolved in ethyl acetate and washed with brine. The organic layer was dried and concentrated to dryness to obtain the title compound (200 mg, 76%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 3.91 (d, 2H), 3.30 (t, 2H), 2.63-2.66 (m, 1H), 1.90-1.96 (m, 2H), 1.67-1.69 (m, 2H), 1.45 (s, 18H).

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; ONO PHARMACEUTICAL CO., LTD.; Imagawa, Akira; Kondo, Takashi; Nishiyama, Taihei; Courtney, Steve; Yarnold, Chris; Ichihara, Osamu; Flanagan, Stuart; US2015/152048; (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. 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

Application of 152120-54-2,Some common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, molecular formula is C14H22N4O4, 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 stirred solution of N,N?-di-Boc-pyrazologuanidine (1,0 g, 3,22 mmol) in dry THF (20 mL) under N2 atmosphere, PPh3 (1,27 g, 4,19 mmol) and crotyl alcohol (0,36 mL, 4,19 mmol) were added. The mixture was cooled to 0 Cand DIAD (0,91 mL, 4,84 mmol) was added dropwise. The mixture was stirred at 0 C for 15 min then at room temperature for 2 h, then it was diluted with AcOEt and washed with water. The aqueous phase was back-extracted with AcOEt. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified with flash chromatography on silica gel, eluting with 10% AcOEt/Hex to give pure compound 9 (0.95 g, 95% yield). 1H NMR (400 MHz CDCl3) delta 7.89 (s, 1H), 7.66 (s, 1H), 6.37 (s, 1H), 5.60 (m, 2H), 4.18 (m, 2H), 1.62 (s, 3H), 1.44 (s, 9H), 1.22 (s, 9H). LC-MS(ES) m/z = 387.1 [M+Na]+, 365.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, its application will become more common.

Reference:
Article; Borgini, Matteo; Orofino, Francesco; Truglio, Giuseppina I.; Balestri, Lorenzo; Botta, Maurizio; Arkivoc; vol. 2019; 4; (2019);,
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

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