Tag: M.W:100-200

Synthetic Route of 20154-03-4, A common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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.

Reference Example 15 Preparation of 2-Chloro-4-(3-trifluoromethylpyrazolyl)benzaldehyde (Compound XVI) 4.08 g (30.0 mmol) of 3-trifluoromethylpyrazol, 4.75 mmol (30.0 mmol) of 2-chloro-4-fluorobenzaldehyde and 4.14 g (30.0 mmol) of potassium carbonate in 30 ml of N,N-dimethylformamide were stirred at 60° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into 100 ml of water, and the organic matters were extracted with 50 ml of ethyl acetate twice. The ethyl acetate layers were combined, washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. The residue afforded 7.18 g of 2-chloro-4-(3-trifluoromethylpyrazolyl)benzaldehyde (yield 87.2percent) as a pale yellow powder, after washed with n-hexane.

The synthetic route of 20154-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US6509354; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 42098-25-9, 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. 42098-25-9 name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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 78 tert-Butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate A solution of 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (1.9 g, 11.77 mmol), 4-(boc-aminomethyl)piperidine (3.78 g, 17.66 mmol) and DIPEA (6.15 mL, 35.31 mmol) in EtOH (20 mL) was heated in a microwave at 130 C. for 1 hr. The solvent was removed under reduced pressure and the residue re-dissolved in DCM. The organic layer was washed with water, passed through a phase separation cartridge and concentrated under reduced pressure. The residue was purified via silica gel column chromatography (0-100% EtOAc/isohexane) to yield tert-butyl (1-(1-methyl-4-nitro-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate as a yellow solid (3.95 g, 98%). To a solution of this solid (3.84 g, 11.30 mmol) in MeOH (125 mL) was added 10% Pd/C (0.42 g, 3.96 mmol) and ammonium formate (2.85 g, 45.2 mmol). The mixture was heated at 80 C. for 2.5 hr. The mixture was concentrated under reduced pressure and the residue was re-dissolved in EtOAc and washed with water. The organic layer was passed through a phase separation cartridge and concentrated under reduced pressure to give tert-butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate as a brown oil (3.49 g, 99%). 1H NMR (400 MHz, CDCl3) delta 7.04 (s, 1H), 4.63 (s, 1H), 3.64 (s, 3H), 3.11-3.07 (m, 6H), 2.67 (s, 2H), 1.77 (d, J=12.8 Hz, 2H), 1.45 (s, 9H), 1.39-1.26 (m, 2H). 1H hidden by water peak.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1-methyl-4-nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (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. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile

General procedure: An equimolar mixture of Int-I (chalcones) and Int-II (5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile) was refluxed in n-butanol for 4-5 h. The completion of reaction was confirmed by Thin Layer Chromatography using (6:4- hexane: ethyl acetate) as a mobile phase. The reaction mixture was then allowed to cool and the resulting solid was filtered and washed with diethyl ether to remove impurities. The procedure was repeated 3-4 times to free the product from impurities.

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:
Article; Baluja, Shipra; Nandha, Kajal; Journal of Molecular Liquids; vol. 201; (2015); p. 90 – 95;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-45-8, name is 4-Bromo-1H-pyrazole, 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 2075-45-8, category: pyrazoles-derivatives

A 100 mL round bottom flask was charged with 4-bromopyrazole (4.41 g, 30 mmol), tetrabutylammonium bromide [(484] mg, 1.5 mmol) and potassium hydroxide pellets (3.37 g, 60 mmol). After the mixture was sonicated for 15 min, benzyl chloride (5.2 [ML,] 45 mmol) was added dropwise and the resulting mixture was stirred overnight. Ethyl ether (20 mL), water (20 mL), and diluted hydrochloric acid (1 [ML,] [10%)] were added under stirring. The organic layer was washed with water [(2X20] mL) and dried over MgS04. The solvent was removed under reduced pressure and the product was purified by flash chromatography on silica gel (hexane/ethyl acetate 10: 1) to provide the desired product as a white solid (6.74 g, 95% yield). Mp [51-52 C] (lit. [44-45 C,] See Jones, R. G. [J.] Am. [CHEM.] Soc. 1949, [71,] [3994).’H NMR] (400 MHz, CDC13) : [8] 7.53 (s, 1H), 7.42-7. 33 (m, 4H), 7.28-7. 22 (m, 2H), 5.29 (s, 2H); [13C] NMR (100 MHz, CDC13) : [6] 140.4, 136.2, 129. 8, 129.4, 128.8, [128.] 3,93. 9, 57.1.

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, 4-Bromo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (2004); 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. 943541-20-6, name is 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 943541-20-6

Quinazolin-6-yl-acetic acid hydrazide (0.032 g, 0.158 mmol) and 3-chloro-6-(l- methyl-lH-pyrazol-4-yl)-pyridazine (0.031 g, 0.158 mmol) were heated to 165C in 5 butanol (2 mL) for five hours. The reaction was cooled to room temperature, evaporated in vacuo and purified via silica gel column chromatography eluting with 5% methanol in dichloromethane to give 0.0031g (7%) of 6-[6-( 1 -methyl- IH- pyrazol^-yO-tl^^triazolo^.S-blpyridazin-S-ylmethyll-quinazoline. 1H NMR (400 MHz, CD3OD) 5 8.45 (s, IH), 8.29 (s, IH), 8.06 (d, 2H, J=9.6Hz), 7.60 (d, 2H, J=9.6Hz), 7.55 (m, IH), 7.17 (d, IH, J==8.0Hz), 6.08 (s, IH), 4.58 (m, 2H), 3.89 (s, 3H). Mass spectrum (LCMS, ESI pos.): Calcd for Ci8H)4N8; found: 343.3 (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 943541-20-6.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/75567; (2007); 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. 21230-43-3, name is Ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 21230-43-3

(1) Synthesis of ethyl 3-chloro-1-methylpyrazole-4-carboxylate: Into a solution of 150 ml of conc. HCl, 50 ml of phosphoric acid (85%), 41.4 g of ethyl 3-amino-1-methylpyrazole-4-carboxylate and 100 ml of water, there was added dropwise a 50 ml of aqueous solution of 18.6 g of sodium nitrite at 0 C. or lower. The reaction mixture was added dropwise into a solution of 90 g of cupric sulfate (pentahydrate) and 60 g of sodium chloride dissolved in 200 ml of water at room temperature. The mixture was heated for an hour at 50 C. and after cooling, followed by extraction with chloroform. After washing with water and drying, evaporation of the solvent gave 44.8 g of ethyl 3-chloro-1-methylpyrazole-4-carboxylate. m.p.: 65-66 C.

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; Nissan Chemical Industries, Ltd.; US4668277; (1987); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 852227-86-2, 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. 852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

10171] Step 4. A mixture ofD-15 (210 mg, 0.78 mmol) and cesium carbonate (765 mg, 2.35 mmol) in DMF (25 mL) was heated to 60 C. with stirring then a solution of 5-(chlorom- ethyl)-1,3-dimethyl-1H-pyrazole (113 mg, 0.78 mmol) in DMF (10 mL) was added drop wise. The reaction mixture was stirred for 1 hour at 60 C. The solids were removed by filtration and the solvent was removed under reduced pressure. Crude D-16 was used as such in the next step.10172] LC-MS: Anal. Calcd. For C18H28N503: 376.22; found 377 [M+H]

The chemical industry reduces the impact on the environment during synthesis 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; McGowan, David; Raboisson, Pierr Jeane-Marie Bernar; Embrechts, Werner; Jonckers, Tim Hugo Maria; Last, Stefaan Julien; Pieters, Serge Maria Aloysius; Vlach, Jaromir; US2014/45849; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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. name: 4-Nitro-1H-pyrazole

4-Nitro-1H-pyrazole 12 (10.0 g, 88.4 mmol) was taken in CH3CN (100 mL) in a 250 mL round bottom flask under N2. To it were sequentially added iodomethane (18.8 g, 132.0 mmol) and K2C03 (30.5 g, 221.0 mmol). The reaction mixture was heated at 100C for 1 6h. The reaction mixture was then poured into ice water (100 g) and extracted with EtOAc (3 x 100 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was further washed with n-pentane to afford 15 as a light yellow solid (10.8 g, 96% yield). ?H NMR (400 MHz, CDC13): 88.11 (s, 1H), 8.05 (s, 1H), 3.96 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2075-46-9, its application will become more common.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 113100-53-1, A common heterocyclic compound, 113100-53-1, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C6H5F3N2O2, 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: Intermediate 5 (1.0 mmol) and 4-dimethylaminopyridine (0.1 mmol) were added to a mixture of the corresponding carboxylic acid 6 (1.3 mmol) and (EDCI, 2 mmol) in CH2Cl2 (20 mL). The reaction system was stirred at room temperature overnight and then diluted with CH2Cl2 (50 mL). The resulting mixture was consecutively washed with 10% citric acid solution and brine. Then the organic phase was dried with sodium sulphate and filtered, and concentrated under reduced pressure. The residue was purified on a silica gel column to afford the title compounds 7-17.

The synthetic route of 113100-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xiong, Li; Zhu, Xiao-Lei; Shen, Yan-Qing; Kandergama Wasala Mudiyanselage Wishwajith, Wickramabahu; Li, Kui; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 424 – 434;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 108161-12-2, A common heterocyclic compound, 108161-12-2, name is 3,5-Dimethyl-1H-pyrazole-4-carbonitrile, molecular formula is C6H7N3, 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.

4,6-dichloropyrimidine (1.27 g, 8.50 mmol), 3,5-dimethyl-1H-pyrazole-4-carbonitrile (1.03 g, 8.50 mmol) and caesium carbonate were dissolved in DMF. The reaction mixture was stirred at room temperature overnight. Water was added and the resulting mixture was stirred at room temperature for 30 min. The precipitate was filtered, washed with water and dried under reduced pressure to afford the desired product 1.06 g (53 % yield), which was used as such in the next step. LC-MS (method 11): Rt = 1.28 min; MS (ESIpos): m/z = 234 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm] : 2.339 (0.76), 2.378 (15.68), 2.403 (1.58), 2.732 (0.44), 2.781 (0.70), 2.826 (16.00), 2.868 (1.38), 2.891 (0.55), 5.754 (0.68), 8.014 (2.62), 9.038 (2.54).

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 AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; KLAR, Juergen; EHRMANN, Alexander; WILLWACHER, Jens; ENGEL, David; DIESKAU, Andre Philippe; KAHNERT, Antje; GROMOV, Alexey; SCHMECK, Carsten; LINDNER, Niels; MUeLLER, Thomas; ANDREEVSKI, Anna Lena; DREHER, Jan; COLLINS, Karl; (861 pag.)WO2018/69222; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics