Day: July 23, 2021

Some common heterocyclic compound, 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, molecular formula is C5H9N3, 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. Recommanded Product: 3524-32-1

General procedure: A solution of equimolar amounts (4.5 mmol) of 1,3-dimethyl-1H-pyrazol-5-amine 3 [18] and substituted phenylisocyanates 4a-g in THF (12 mL) was stirred at room temperature for 24 h. The solid residue was filtered, washed with 1 mL of ethyl acetate, and then crystallized from a suitable solvent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3524-32-1, its application will become more common.

Reference:
Article; Raimondi, Maria Valeria; Maggio, Benedetta; Raffa, Demetrio; Plescia, Fabiana; Cascioferro, Stella; Cancemi, Gabriella; Schillaci, Domenico; Cusimano, Maria Grazia; Vitale, Maria; Daidone, Giuseppe; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 64 – 71;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, A common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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-Aminopyrazole (111 mg, 1.00 mmol) in DMF (3.3 mL) in a 20 mL vial was added 2,4-Dichloro-6-trifluoromethylquinazoline (200 mg, 1.00 mmol) and DIEA (258 mg, 2.00 mmol, 0.348 mL). The mixture was heated at 100 C overnight, cooled to rt and poured into water. The precipitate that was formed was filtered and washed with water, dried on the filter for 1 h then in a desiccator overnight to give 227 mg of a grey solid that was used as is in the next step. MS (ES+) m/e 314/316 (M+H)+.

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; KADMON CORPORATION, LLC; LIU, Kevin G.; OLSZEWSKI, Kellen L.; KIM, Ji-In; POYUROVSKY, Masha V.; MORRIS, Koi; YU, Xuemei; LAMARQUE, Christophe; (0 pag.)WO2020/5935; (2020); 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 113100-53-1 as follows. Computed Properties of C6H5F3N2O2

EXAMPLE 1 This Example illustrates the preparation of 1-methyl-3-trifluoromethyl-1 H-pyrazole-4- carboxylic acid (theta-dichloromethylidene-benzonorbornene-S-yOamide (compound A-1.4):theta-Dichloromethylene-S-amino-benzonorbomene (175 mg, 0.729 mmol, prepared as described in Example 6) in dichloromethane (10ml) was reacted with 1-methyl-3- trifluoromethyl-1 H-pyrazole-carboxylic acid (170mg, 0.874 mmol, 1.2 eq.) in the presence of bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride (278 mg, 1.09 mmol, 1.5 eq.) and triethylamine (184 mg, 1.821 mmol, 2.5 eq.) at ambient temperature under stirring for 23 hours. The reaction mixture was extracted with saturated sodium bicarbonate solution and saturated brine, dried over Na2SO4 and purified on silica gel in ethyl acetate-hexane-(1 :1). 210 mg (69% of theory) of i-methyl-S-trifluoromethyl-I H-pyrazole^-carboxylic acid (9- dichloromethylidene-benzonorbornene-5-yl)amide (compound A-1.4, m.p. 179-181 0C) was obtained.

According to the analysis of related databases, 113100-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2008/131901; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, 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. Recommanded Product: 1260243-04-6

To a mixture of ethyl 5-amino- lH-pyrazole-4-carboxylate (150.00 g, 1.08 mmol) and ethyl (E)-3-ethoxyprop-2-enoate (292.16 g, 2.03 mol) in DMF (3.2 L) was added Cs2C03 (656.77 g, 2.02 mol) in one portion at 20 °C under N2. The mixture was stirred at 110 °C for 6 h. TLC (PE: EtOAc=l : 1) showed the reaction was completed. The mixture was cooled to 20 °C and filtered through a celite pad. The filter cake was washed with ethyl acetate (3X30 mL). The filtrate was added to H20 (2 L) and acidified with HOAc to pH=4. The resultant precipitate was filtered to afford A-1-7 (173.00 g, 834.98 mmol, 86.36percent yield) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta 8.54 (d, 7=7.91 Hz, 1H), 8.12 (s, 1H), 6.13 (d, 7=7.91 Hz, 1H), 4.27 (q, 7=7.11 Hz, 2H), 1.28 (t, 7=7.09 Hz, 3H).

The synthetic route of Ethyl 5-amino-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TP THERAPEUTICS, INC.; CUI, Jingrong J.; LI, Yishan; ROGERS, Evan W.; ZHAI, Dayong; DENG, Wei; UNG, Jane; (170 pag.)WO2017/4342; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 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.

The synthetic route of 120068-79-3 has been constantly updated, and we look forward to future research findings.

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

Related Products of 25016-20-0, 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 25016-20-0 as follows.

To a solution of 1 -methyl- 7/-/-pyrazole-3-carboxylic acid (50 mg, 0.397 mmol) and diisopropylethylamine (154 mg, 1 .19 mmol) in tetrahydrofuran (4.0 ml_) at 20 C was added 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (226 mg, 0.595 mmol). The reaction mixture was stirred for 20 minutes before a solution of 3-((6-aminopyridin-3-yl)methyl)-5-fluorobenzonitrile (90 mg, 0.397 mmol) in tetrahydrofuran (1 .0 mL) was added. The reaction solution was stirred at 20 C for 16 h. The volatiles were removed under reduced pressure and the crude residue was added to a mixture of dichloromethane (50 mL) and water (50 mL). The combined organic layers were collected, dried over sodium sulfate, filtered and concentrated. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified via prep-HPLC (Boston C18 21 *250 mm 10 pm column; acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3-cyano-5-fluorobenzyl)pyridin-2-yl)-1 -methyl- 7/-/-pyrazole-3-carboxamide as a white solid (29.3 mg, 0.087 mmol, 22%). 1 H NMR (400 MHz, Dimethylsulfoxide-c/e) d 1 0.48 (s, 1 H), 8.41 (s, 1 H), 8.32 (d, J = 1 .8 Hz, 1 H), 8.10 (d, J = 8.9 Hz, 2H), 7.77 – 7.66 (m, 2H), 7.57 (d, J = 9.4 Hz, 1 H), 4.02 (s, 2H), 3.87 (s, 2H); LCMS (ESI) m/z: 336.1 [M+H]+.

According to the analysis of related databases, 25016-20-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 4149-06-8,Some common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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: To a mixture of 3-amino-1-phenyl-2-pyrazolin-5-one 1 (0.35 g, 2 mmol), dimedone 2 (0.28 g, 2 mmol), and aldehyde 3 (2 mmol) in 15 mL ethanol, 0.14 g (0.004 mol %) H3PW12O40 was added. The reaction mixture was refluxed at 80 C for the time reported in Table 1. Reaction progress was monitored by TLC using EtOAc-hexane (60:40) as eluent. After reaction completion, 50 mL cold water was added to the reaction mixture. The crude product was recrystallized using methanol to obtain the pure product.

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zahedifar, Mahboobeh; Shojaei, Reza; Sheibani, Hassan; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 873 – 882;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-13-1, 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. 288-13-1, name is 1H-Pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(1) 6.81 g (0.1 mol) of pyrazole was dissolved in 50.0% of hydrobromic acid (161.80 g, containing 1.0 mol of hydrogen bromide).Under stirring, the temperature is controlled at 5-15 C., and a 25.0% solution of potassium dichromate 47.07 g is added dropwise.After completion of the dropwise addition, the reaction temperature was controlled at 5-15 C. to allow the reaction system to undergo a bromination reaction. During the reaction, samples were taken at regular intervals and detected by high performance liquid chromatography.When it was detected that the mass of 3-bromopyrazole in the reaction system accounted for 93.0% of the total mass of organic matter in the reaction system, 4.31 g (0.06 mol) of ferrous oxide was added to terminate the reaction to obtain a feed liquid containing 3-bromopyrazole; (2) Add 73.5 g of chlorobenzene to the feed solution, stir and extract for 2 hours, let stand for 1 hour, take the organic phase and allow it to cool down to -15C to -5C,The solids were analyzed by elution from the organic phase. The resulting 12.20 g of solid was 3-bromopyrazole. The yield was calculated to be 83%. After the determination, the main content was 98.5%.

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, 1H-Pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Tianxin Chemical Co., Ltd.; Ju Youguo; Zhao Benteng; Wang Zewu; Yang Hanhua; Zhang Zhaoyuan; Liu Jian; Gong Fangxin; (6 pag.)CN107954913; (2018); A;,
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. 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Safety of 5-Methyl-1H-pyrazol-3-amine

Intermediate 11: (2-Chloropyrimidin-4-yl)-(5-methylpyrazol-3-yl)amine.; A mixture of 2,4-dichloropyrimidine (0.967 g, 6.49 mmol), 3-amino-5-methylpyrazole (0.63 g, 6.40 mmol), and ethyldiisopropylamine (2.8 mL, 16.22 mmol) in ethanol (13 mL) was stirred at -10 C. for 2 h, then at r.t. overnight, and finally at 50 C. for 3.5 h. The mixture was concentrated to a total volume of approximately 10 mL. Upon repeated addition of diethylether, (2-chloropyrimidin-4-yl)-(5-methylpyrazol-3-yl)amine (0.258 g, 1.23 mmol, 19%) was obtained as colourless crystals. LC/ESI-MS: m/z=210 [M(35Cl)+H]+; m/z=208 [M(35Cl)-H]-; Rt=230 min.

The synthetic route of 31230-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 4SC AG; US2006/142570; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 2075-45-8, These common heterocyclic compound, 2075-45-8, name is 4-Bromo-1H-pyrazole, 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 4-bromo-pyrazole (10.44 g, 71.03 mmol) in anhydrous DMF (96 mL), cooled to 0C, was slowly added NaH (60% in mineral oil) (3.13 g, 78.133 mmol). The solution was stirred for 1 hour at 0C. 4-Methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (19.82 g , 71.03 mmol) was added slowly and the reaction was heated to 100C overnight or until consumption of the pyrazole by NMR. The reaction was cooled to room temperature and water added (20 mL) followed by extraction with EtOAc. The combined extracts were washed with saturated aqueous NaCI (4 x 20 mL), dried with Na2SO4 and concentrated to afford 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as an orange oil. The oil was purified using silica gel chromatography eluting with 10% EtOAc/hexanes to 25% EtOAc/hexanes to provide 4-(4-bromo-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester as a white solid (10.55 g, 45% yield) with a R^= 0.4 (25% EtOAc/hexanes, using iodine as the stain). 1H NMR (CDCI3, 400 MHz) 8 7.46 (s, 1H), 7.43 (s, 1H), 4.23 (m, 3H), 2.88 (m, 2H), 2.10 (m, 2H), 1.88(m, 2H), 1.47(s, 9H).

Statistics shows that 4-Bromo-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 2075-45-8.

Reference:
Patent; PFIZER INC.; WO2006/21881; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics