Tag: M.W:200-300

Application of 285984-25-0, 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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of compounds 10a-d or compounds 17a-d (1.0 mmol) in dichloromethane (10 mL) was slowly added to a stirred solution of triphosgene (109 mg, 0.36 mmol) in dichloromethane (50 mL) over a period of 30 min using a syringe. After stirring for a further 30 min, a solution of compound 25a-r (0.6 mmol) and triethylamine (0.4 mL, 2.77 mmol) in dichloromethane (10 mL) was added in one portion. The reaction mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction was poured into water (50 mL) and extracted three times with dichloromethane. The organic layer was washed with water (5 mL), sat. NaCl solution (5 mL), anddried over Na2SO4. After evaporation of solvent under vacuum, the residue was purified by silica gel chromatography to give the desired chromanylurea or 2H-chromenyl urea compounds.

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-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Xingzhou; Zhou, Xinming; Zhang, Jing; Wang, Lili; Long, Long; Zheng, Zhibing; Li, Song; Zhong, Wu; Molecules; vol. 19; 2; (2014); p. 2004 – 2028;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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. Formula: C9H12N2O4

Example 27; Preparation of (5R, 6Z)-7-oxo-6- [ (4-oxo-6, 7-dihydro-4H-pyrazo . o [5, 1-c] [1, 4] oxazin-2- yl) methylene]-4-thia-1-azabicyclo [3. 2. 0] hept-2-ene-2-carboxylic Acid. Step 1: Diethyl 1- (2-frtert-butyl (dimethvl) silvlloxylethyl)-1H-ayrazole-3, 5- dicarboxvlate To a solution of diethyl 3, 5-pyrazoledicarboxylate (2.17 g, 10 mmol) in acetonitrile (10 ml), under nitrogen, was added potassium carbonate (2.07 g, 15 mmol), and 2- bromoethoxy-t-butyldimethylsilane (2.90 g, 12 mmol). The mixture was stirred at reflux for 18 hr. It was then cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered through Magnesol. The filter pad was eluted wtih 2 x 10 mi of ethyl acetate, and the combined filtrate was evaporated. The residue was dissolved in hexanes and passed through a column of silica gel (70 g). After eluting with hexanes (100 ml), the column was eluted with ethyl acetate. The ethyl acetate eluent was evaporated to give 3.71 g of a colorless oil ; MS m/e 371 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 37687-24-4, its application will become more common.

Reference:
Patent; WYETH; WO2003/93277; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1280210-79-8, 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. 1280210-79-8 name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, 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.

To a solution of tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (15.0 g, 71.8 mmol) in DMF (150 mL) was added NaH (60% in mineral oil) (8.6 g, 215.4 mmol) while the reaction mixture was cooled with an ice bath. When the addition was complete, the resulting mixture was allowed to warm to room temperature and was stirred at room temperature for 30 min. At this point, l-bromo-2- methoxyethane (19.8 g, 143.6 mmol) was added into the reaction mixture, and stirring was continued at room temperature for 2 h. The reaction mixture was then quenched with water (300 mL), and extracted with EtOAc (150 mL x 3). The combined organic layer was washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 122 and 122-A (19.0 g, 99%) as a colorless oil. MS 268.2 [M + H]+. [0072] Synthesis of 123 and 123-A. To a solution of 122 and 122-A (6.5 g, 24.3 mmol) in DCM (60 mL) cooled with an ice bath was added TFA (30 mL). The reaction mixture was stirred at room temperature for 1 h, whereupon the solvent was removed in vacuo to give 123 and 123-A as a crude product mixture which was used directly in the next step without further purification. MS 168.1 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; RODIN THERAPEUTICS, INC; FULLER, Nathan, Oliver; LOWE, John, A.; (45 pag.)WO2019/32528; (2019); 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. 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate, A new synthetic method of this compound is introduced below., name: Ethyl 3-phenyl-1H-pyrazole-5-carboxylate

A mixture of ethyl 3-phenyl-lH-pyrazole-5-carboxylate (70.0′ g) , 2, 4-dichlorobenzyl chloride (69.6 g) , potassium carbonate (53.7 g) and N,N-dimethylformamide (400 ml) was stirred at room temperature for 15 hr, the reaction mixture was concentrated, and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSCU) / and concentrated. The residue was crystallized from ethyl acetate- hexane to give ethyl 1- (2, 4-dichlorobenzyl) -3-phenyl-lH- pyrazole-5-carboxylate (61.0 g, yield: 50%) as brown crystals, melting point 104-1070C.

The synthetic route of 13599-12-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2007/18314; (2007); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1105039-93-7, 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 1105039-93-7 as follows.

A solution of l-(4-methoxybenzyl)-lH-pyrazole-4- carboxylic acid (34.4 mmol, 8.00 g), oxalyl chloride (68.9 mmol, 5.92 mL) and a drop of DMF in DCM (80 mL) was stirred for 1 h at rt. After evaporation, the crude product was dissolved in DCM (30 mL) and was added at 0C to a solution of Nu,Omicron- dimethylhydroxylamine hydrochloride (103 mmol, 6.31 g) in DCM (100 mL), followed by Et3N (138 mmol, 19.2 mL). The reaction mixture was stirred for 1 h at rt. The reaction was quenched with a saturated aqueous solution of Na2C03 (300 mL) and the aqueous phase was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated to dryness to yield the title compound (33.8 mmol, 9.30 g, 98%) as a beige solid.UPLC-MS: RT = 0.72 min; MS m/z ES+= 276.

According to the analysis of related databases, 1105039-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA S.A.; JONES, Philip; MERCK SHARP & DOHME CORP.; TANG, Lam; BOLEA, Christelle; CELANIRE, Sylvain; LIVERTON, Nigel, J.; WO2012/9001; (2012); 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 149739-65-1 as follows. COA of Formula: C9H7BrN2

3-(3-Bromo-phenyl)-1H-pyrazole (17 g; 60.97 mmol; 1.00 eq.) dissolved in THF (5 mL) was added dropwise to a suspension of Sodium hydride (2.44 g; 60.97 mmol; 1.00 eq.) in THF (500 mL) maintained at 0C. The reaction mixture was stirred for 30 min before the dropwise addition of lodomethane (8.03 mL; 122 mmol; 2.00 eq.). It was then allowed to warm to RT and stirred for another 4h. Ice was added to quench the reaction and the mixture was extracted with ethyl acetate (30 mL x 2). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound as a brown liquid (14.5 g, 99%). LC/MS: (max plot) 99 %; (254nm) 99 %; Rt 4.1 min; 239.0 (M+1).

According to the analysis of related databases, 149739-65-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Patent GmbH; JORAND-LEBRUN, Catherine; JONES, Reinaldo; (112 pag.)EP3092225; (2019); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 18048-64-1, 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. 18048-64-1, name is 1-(3,4-Dimethylphenyl)-3-methyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

Example 22; 3′- IN’-[ 1-(3,4-Dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]- hydrazino}-2′-fluoro-biphenyl-3-carboxylic acid (Compound 122) was prepared as in Scheme III. 1H NMR (500MHz, Acetone-d6) 8 8.17 (t, J=1.7 Hz, 1H), 8.10 (ddd, J=7.7, 1.7,1.2 Hz, 1H), 7.81 (ddd, J=7.7, 1.7,1.2 Hz, 1H), 7.72 (m, 1H), 7.67 (t, J=7.7 Hz, 1H), 7.62 (d, J=1.9 Hz, 1H), 7.58 (m, 1H), 7.57 (m, 1H), 7.52 (m, 1H), 7.40 (m, 1H), 7.19 (d, J=8.2 Hz, 1H), 2.29 (s, 3H), 2.25 (s, 3H), 2.13 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 1-(3,4-Dimethylphenyl)-3-methyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LIGAND PHARMACEUTICALS INC.; WO2005/118551; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 741717-63-5, 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. 741717-63-5, name is Ethyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl l-phenyl-3- (trifluoromethyl) -IH- pyrazole-4-carboxylate (0.800 g, 2.81 mmol) in EtOH (20 mL) and THF (5 mL) was added 2M aqueous sodium hydroxide (1.69 mL, 8.44 mmol) . The mixture was heated to reflux until TLC indicated completion, cooled to room temperature, and concentrated in vacuo. The residue was dissolved in water and washed with ether. The aqueous layer was then adjusted to pH~4 with 10% HCl. The solid was collected by filtration and dried under vacuum to give l-phenyl-3- (trifluoromethyl) -lH-pyrazole- 4-carboxylic acid (0.560 g, 78%) as a white powder: 1H NMR (400 MHz, DMSO-d6) delta 7.47 (m, IH), 7.58 (m, 2H), 7.94 (m, 2H), 9.24 (bs, IH); m/z (APCI neg) 254.9 (100%) [M-H] .

The chemical industry reduces the impact on the environment during synthesis Ethyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11130; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 106368-32-5, A common heterocyclic compound, 106368-32-5, name is 5-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C11H10N4O2S, 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: A mixture of 5-amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazol-4-carbonitrile 5 (1.113 g, 5 mmol), the appropriate aldehyde (6, 5 mmol), and few drops of ethanol was added to morpholinium hydrogen sulphate (7, 0.4 g, 2 mmol). The mixture was heated in an oil bath for 5 h at 100 C. After completion of the reaction which was monitored by TLC, the solid product was filtered and crystallized from ethanol.

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; Abdellatif, Khaled R.A.; Elsaady, Mohammed T.; Abdel-Aziz, Salah A.; AbuSabah, Ahmed H.A.; Letters in drug design and discovery; vol. 14; 8; (2017); p. 930 – 937;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 89607-15-8, name is 3-Bromo-1-methyl-4-nitro-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 89607-15-8, Product Details of 89607-15-8

Step 5: Into a 100 mL round bottom flask containing a solution of 3-bromo-1-methyl-4-nitro- 1H-pyrazole (1.0 g) in ethyl acetate (50 mL) at room temperature was added Raney Nickel (700 mg) and the reaction mixture was stirred at room temperature for 16 h under hydrogen atmosphere. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by flash chromatography eluting with ethyl acetate in petroleum ether (40-50%) to afford 3-bromo-1-methyl-1H-pyrazol-4-amine as a liquid. 1H NMR (CD3OD, 400 MHz): delta 7.18 (s, 1H), 3.77 (s, 3H). MS calc?d [M+H]+ 176.0, found 176.2

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; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (94 pag.)WO2016/144847; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics