Category: pyrazoles-derivatives

Reference of 2033-45-6, 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. 2033-45-6, name is 3,5-Dimethyl-4-iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of pyrazole (2.04g, 0.03mol) in freshly distilled THF (20mL) was added to a stirred suspension of sodium hydride (60%, 2.04g, 0.03mol) in 20mL THF at room temperature. After 1h, Cyanuric chloride (1.85g, 0.01mol) in THF (15mL) was added to the above solution and white precipitate was formed. After being stirred and heating at 70C for 5h, the solution was filtered off, the filtrate evaporated on a steam bath, and then washed with hot-water. 2,4,6-tri(1H-pyrazol-1-yl)methyl)-1,3,5-triazine.

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, 3,5-Dimethyl-4-iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Ji-Xiao; Zhu, Zi-Ran; Bai, Feng-Ying; Wang, Xin-Yu; Zhang, Xiao-Xi; Xing, Yong-Heng; Polyhedron; vol. 99; (2015); p. 59 – 70;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 288148-34-5, These common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, 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-(5-fluoro-lH-indol-3-yl)-iV’-(4-piperazin-l-ylphenyl)pyrimidin-2-amine (20 mg, 0.051 mmol) in dimethylforamide (1 mL), were added l-methyl-lH-pyrazole-4-sulfonyl chloride (9.3 mg, 0.051 mmol), triethylamine (31.3 mg, 0.309 mmol), and 4-dimethylamino pyridine (cat.). The solution was allowed to stir for 12 hr. After completion of the reaction, the reaction mixture was concentrated and purified by reverse phase chromatography (100% H2O to 100% MeCN) to afford ^(S-fluoro-lH-indol-S-y^-N^-f^tCl-methyl-lH-pyrazoM- yl)sulfonyl]piperazin-l-yl}phenyl)pyrimidin-2-amine as a mono trifluoroacetic acid salt. LRMS m/z (M+H) Calcd: 533.2, found: 533.1.

The synthetic route of 288148-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2007/149427; (2007); A2;,
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 478968-48-8 as follows. HPLC of Formula: C7H10N2O3

Step 4. Ethyl 3-methoxy-l-pyrimidin-2-yl-lH-pyrazole-4-carboxylate; Sodium hydride (60% in mineral oil, 528 mg, 13.2 mmol) is added portion wise to a solution of ethyl 3-methoxy-lH-pyrazole-4-carboxylate (1.5 g, 8.81 mmol) in 40 mL of THF at RT. Evolution of H2 (g) is observed. After about 5-10 min, 2-chloropyrirnidine (1.0 g, 8.81 mmol) is added, and the resulting reaction mixture is stirred at reflux for 15 h. After cooling to RT, the reaction is quenched with 10 mL of sat. NH4Cl and 10 mL of water and extracted with CH2Cl2 (2 x 40 mL). The combined organic extracts are dried (Na2SO4), filtered, and evaporated in vacuo to give a brown solid. Purification by silica gel column chromatography (gradient from 50% EtOAc/hexane to EtOAc) affords the title compound as a fluffy white solid.

According to the analysis of related databases, 478968-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2009/12482; (2009); 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. 3469-69-0, name is 4-Iodopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 3469-69-0

4-Iodo-l-(4-methoxybenzyl)-lH-pyrazole According to Scheme 9 Step 1 : A suspension of 4-iodo-lH-pyrazole (26.3 mmol, 5.11 g), l-(chloromethyl)-4-methoxybenzene (29.0 mmol, 3.95 mL) and K2CO3 (39.5 mmol, 5.46 g) in acetonitrile (150 mL) was heated at 6O0C overnight. The reaction mixture was cooled to room temperature and was filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using DCM as eluent to afford 4-iodo-l-(4-methoxybenzyl)-lH-pyrazole (23.2 mmol, 7.3 g, 88%) as a yellow solid. UPLC-MS: RT = 1.02 min; MS m/z ES+= 315.

According to the analysis of related databases, 3469-69-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA S.A.; BOLEA, Christelle; WO2010/79239; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 852443-61-9, name is 3-(Trifluoromethyl)-1H-pyrazol-5-amine, molecular formula is C4H4F3N3, 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. Application In Synthesis of 3-(Trifluoromethyl)-1H-pyrazol-5-amine

Tert-butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-l-carboxylate (1.0 g, ca. 2.77 mmol), 3- (trifluoromethyl)-lH-pyrazol-5 -amine (0.28 g, 1.85 mmol) and potassium phosphate (0.79 g, 3.70 mmol) were suspended in 1 -methoxy-2-propanol (10 ml) in a 20 ml microwave vial. The vial was capped and the mixture was heated in a microwave to 180C for 15 min. After cooling to RT, the solvent was evaporated and the residue was treated with water and ethyl acetate. After separation of the layers the aqueous phase was neutralized by addition of HQ 4N and extracted with ethyl acetate. The collected organic layers were dried over magnesium sulfate, filtered and evaporated. The crude product was purified by preparative HPLC (Method 1A). The combined product fractions were neutralized with a 33% ammonia solution and then acetonitrile was evaporated. The aqueous phase was extracted with ethyl acetate and the collected organic fractions were dried over sodium sulfate, filtered and evaporated under vacuo to yield the title compound (132 mg, 19% of theory). LC-MS (Method IB): Rt = 1.06 min, MS (ESIPos): m/z = 387 [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 852443-61-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-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. Safety of Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate

11512] A solution of ethyl 5-amino-i-phenyl-1H-pyra-zole-3-carboxylate (CAS: 866837-96-9, 300 mg, 1.3 mmol) in THF (6.5 mE), under nitrogen atmosphere was cooled down to -78 C. Diisobutylaluminum hydride (1 M in toluene, 2.9 mE, 2.9 mmol) was added dropwise to the solution, and the stirring at -78 C. was continued for 1 hour. Methanol was added, and the reaction mixture was stirred for 30 minutes warming to RT. DCM was added, and the organic phase was washed with water. The organic phase was separated using a phase separator and concentrated under reduced pressure. The titled compound was used as such without any further purification.

The synthetic route of 866837-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Akkari, Rhalid; Alvey, Luke Jonathan; Bock, Xavier Marie; Claes, Pieter Isabelle Roger; Cowart, Marlon D.; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Gosmini, Romain Luc Marie; Housseman, Christopher Gaetan; Jansen, Koen Karel; Ji, Jianguo; Kym, Philip R.; Lefrancois, Jean-Michel; Mammoliti, Oscar; Menet, Christel Jeanne Marie; Newsome, Gregory John Robert; Palisse, Adeline Marie Elise; Patel, Sachin V; Pizzonero, Mathieu Rafael; Shrestha, Anurupa; Swift, Elizabeth C.; Van der Plas, Steven Emiel; Wang, Xueqing; (454 pag.)US2017/101406; (2017); 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. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H15N3O2

To a solution of 2-(3-bromophenyl)acetic acid (0.5g, 2.32mmol) in DCM (20mL) was added EDCI (0.88g, 0.4.65mmol) at 0 C followed by DIPEA (1.l2mL, 6.97mmol) and finally added tert-butyl 3-amino-5-methyl- 1 H-pyrazole- 1 -carboxylate (0.4g, 2.O9mmol). The reaction mass was stined for 12h at room temperature. The reaction mixture was quenched with ice-water and diluted with DCM. The aqueous layer was separated and extracted with ethyl acetate (2x25mL). The combined organic phase was washed with brine, dried over Na2504, filtered and concentrated under reduced pressure and purified by eluting with 20% ethyl acetate-hexane in combiflash to afford the title compound (0.3g, 60%). LCMS: mlz = 395.9 (M+H).

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 578008-32-9.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; PODDUTOORI, Ramulu; PANDIT, Chetan; MUKHERJEE, Subhendu; GOSWAMI, Rajeev; (126 pag.)WO2016/193939; (2016); 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. 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C5H9N3O2S

Step A: Preparation of3-Chloro-N,N-dimethyl- 1 H-pyrazole- 1-sulfonamideTo a solution of N-dimethylsulfamoylpyrazole (188.0 g,1.07 mol) in dry tetrahydrofuran (1500 mE) at 78 C. wasadded dropwise a solution of 2.5 M n-butyllithium (472 mE,1.18 mol) in hexane while maintaining the temperature below65 C. Upon completion of the addition the reaction mixturewas maintained at 78 C. for an additional 45 minutes, afterwhich time a solution of hexachloroethane (279 g, 1.18 mol)in tetrahydrofuran (120 mE) was added dropwise. The reac40 tion mixture was maintained for an hour at 78 C., warmedto 20 C. and then quenched with water (1 E). The reactionmixture was extracted with methylene chloride (4×500 mE);the organic extracts were dried over magnesium sulfate andconcentrated. The crude product was further purified by chro45 matography on silica gel using methylene chloride as eluentto afford the title product compound as a yellow oil (160 g).?HNMR(CDC13) oe 3.07 (d, 6H), 6.33 (s, 1H), 7.61 (s, 1H).

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; E I DU PONT DE NEMOURS AND COMPANY; Berger, Richard Alan; Annan, Isaac Billy; Lahm, George Philip; Flexner, John Lindsey; Selby, Thomas Paul; Stevenson, Thomas Martin; US9173400; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1280210-79-8, A common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 stirred solution of feri-butyl 2,6-dihydropyriOlo[3,4-c]pyrazole-5(4H)- carboxylate (Step A of Intermediate 7) (35 g, 167 mmol) in DMF (500 mL) at 0 C under N2 was added sodium hexamethyldisilazide in THF (351 mL, 351 mmol) and the mixture was stirred at 0 C for 30 min. Isobutylene oxide (74.3 mL, 836 mmol) was then slowly added. The solution was stirred at 0C for 0.5 h and then stirred at room temperature for 1 h. The solution was heated to 80C for 100 min in a microwave oven, cooled to room temperature and evapoarted under vacuum. The residue was purified by column chromatography on silica gel, eluting with a gradient of 0% to 6% CH2Cl2 MeOH (containing 10% NH4OH) to give a mixture of two regioisomers. The mixture of two regioisomers A and B was resolved by chromatography on a ChiralPak AD-H column eluting with 4-40% MeOH/C02 to give isomer A as the faster eluting isomer and isomer B as the slower eluting isomer. NMR (500 MHz, CD3OD) for isomer B: 57.42 (d, 1H); 4.42 (s, 2H); 4.41 (s, 2H); 4.07 (s, 2H); 1.51 (d, 9H); 1.16 (s, 6H). LC-MS: 226.27 (M+l -56).The desired isomer B was treated with 1 : 1 TF A/CH2CI2 for 1 h to give the title compound. NMR (500 MHz, CD3OD): 67.55 (s, 1H); 4.43 (s, 2H); 4.39 (s, 2H); 4.10 (s, 2H); 1.17 (s, 6H). LC-MS: 182.31 (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.; HICKS, Jacqueline, D.; BIFTU, Tesfaye; CHEN, Ping; QIAN, Xiaoxia; WILKENING, Robert, R.; WO2011/146358; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1222174-92-6, 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. 1222174-92-6, name is Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of intermediate 2a (506 mg) in dioxane (10 mL) was treated with LiOH solution (2 M, 1 mL) and the mixture was stirred at 70 C. for 1 h. HCl (1 M) was added and the mixture was extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure to yield the desired compound (84% yield). [0358] LC-MS (Method 2): m/z [M+H]+=205.0 (MW calc.=205.01); Rt=0.31 min.

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

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics