Category: pyrazoles-derivatives

Related Products of 162758-35-2, The chemical industry reduces the impact on the environment during synthesis 162758-35-2, name is 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, I believe this compound will play a more active role in future production and life.

Scheme 3 depicts the conversion of the carboxylic acid from Scheme 1 to its acid chloride using thionyl chloride or oxalyl chloride in dichloroethane at ambient to elevated temperatures followed by treatment with an amine such as alanine ethyl ester (A=methyl, n=0) in the presence of triethylamine to afford the amide ester (step a). Hydrolysis of the ester with lithium hydroxide in aqueous THF solution and acidification with dilute hydrochloric acid solution should yield the amide carboxylic acid (step b). This acid can be further treated with Boc anhydride (Boc2O) in THF in the presence of pyridine, followed by a solution of ammonia in THF at 0 degrees to ambient temperature to yield the carboxamido compound (step c).

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, 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JENRIN DISCOVERY; US2007/213302; (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. 13745-17-0, name is 4-Bromo-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Formula: C4H3BrN2O2

Ste 2: (0585) Preparation of 4-bromo-N-(2,2-dimethoxyethyl)-1H-pyrazole-3-carboxamide: (0586) [00242] To a stirred solution of 4-bromo-1H-pyrazole-3-carboxylic acid (3.4 g, 17.8 mmol) in dichloromethane (100 mL) were added triethylamine (12.42 mL, 89.00 mmol) and 2,2-dimethoxyethanamine (2.9 mL, 26.70 mmol) at room temperature. The reaction mixture was cooled to 0 C and 1-propanephosphonic anhydride solution (T3P) (15.89 mL, 26.70 mmol, 50% in ethyl acetate) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water (200 mL) and extract with dichloromethane (3 x 100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound 4-bromo-N-(2,2-dimethoxyethyl)-1H-pyrazole-3- carboxamide (3.6 g, crude) as a white solid. Calculated (M-H): 276.01; Found (M-H): 276.0.

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; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 155377-19-8,Some common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, molecular formula is C7H7F3N2O2, 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 ethyl 3- {trifluoromethyl) -lH-pyrazole-4- carboxylate (0.208 g, 1.0 mmol) in DMF were added lH-indol-5- ylboronic acid (0.322 g, 2.00 mmol), Cu(OAc)2 (0.136 g, 0.75 rninol)/ and pyridine (0.162 ml, 2.00 mmol) and the mixture was stirred at room temperature for 3 days . The mixture was diluted with DCM and filtered through a pad of silica gel. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (3:1 hexanes/EtOAc) to give ethyl 1- (lH-indol-5-yl) -3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (0.313 g, 97%) as a solid: 1H NMR (CDCl3) delta 1.39 (t, 3H7 J = 7.0 Hz), 4.37 Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11131; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1384973-12-9, name is 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, 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. Formula: C4H3BrN4

General procedure: A mixture of halide (1 .0 eq.), boronic acid or pinacol ester (1 .5 eq.) and potassium carbonate (2.0 eq.) in 1,4-dioxane and water (3:1, 0.1 M)was degassed by bubbling nitrogen through it for 15 mi 1,1- bis(diphenylphosphino)ferrocene-palladium(ll) dichloride dichloromethane complex (0.05 eq.) was added and the mixture was degassed again by bubbling nitrogen through it for 15 mm. The mixture was then heated under microwave irradiation at 120-140 C for 60-90 mm. The reaction mixture was either purified by SCX SPE cartridge and used as such or purified using the following procedure, unless stated used crude. The mixture was filtered through a pad of Celite. The cake was rinsed with DCM. Water was added to the filtrate and the layers were partitioned. The aqueous layer was extracted with DCM (x2). The combined organic extracts were filtered over phase separator and then concentrated under reduced pressure to give a dark solid. Further purification by flash column chromatography gave the desired compound.; General procedure D, 5-fluoro-N-[[2-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl]methyl]-2-methoxy-benzamide (1 .65 mmol) and 5-amino-3-bromo-1 H-pyrazole-4-carbonitrile (1.34 mmol) gave, after purification, titled compound (0.78 mmol). UPLC-MS (ES, Short acidic): 1.67 mi m/z 384.0 [M+H]

The synthetic route of 1384973-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, 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 660845-30-7, Product Details of 660845-30-7

In a 500 ml flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carbaldehyde are added to 30 ml of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 ml of water is added to the reaction mixture, followed by 103 ml of a 30% solution of hydrogen peroxide in water, whilst keeping the temperature below 37 C. After the end of the addition, the reaction mixture is stirred at 50 C for 7 hours. Once the reaction mixture is back to room temperature, the two phases are separated and the organic phase is extracted with 100 ml of water. The combined aqueous phases are acidified to pH 2 with aqueous hydrochloric acid. The resulting white precipitate is filtered, washed twice with 20 ml of water, and dried to yield 3.2 g of 5-chloro-3-(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxylic acid as a white solid. H NMR (400 MHz, DMSO-c/6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1 H, JHF = 53.60 Hz)13.19 (s, 1 H); IR (KBr) : 1688 cm”1 (C=0); 2200-3200 cm”1 broad (hydrogen bond).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; DAHMEN, Peter; DESBORDES, Philippe; GARY, Stephanie; HADANO, Hiroyuki; VORS, Jean-Pierre; WACHENDORFF-NEUMANN, Ulrike; WO2012/52491; (2012); A2;,
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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

Dissolve 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-tert-butyl carboxylate 3a (2.8 g, 13.5 mmol) in acetonitrile (50 mL) and add 3-chloro Benzyl bromide (3.3 g, 16.2 mmol) and cesium carbonate (32.5 g, 47 mmol) were vented 3 times under nitrogen and placed in an 80 C oil bath for 3 hours. The reaction solution was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (petroleum ether: ethyl acetate = 2: 1) to obtain 2-(3-chlorobenzyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-tert-butyl carboxylic acid 3b (4.1 g, yellow oil), yield 91%.

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; Shanghai Meidixi Bio-pharmaceutical Co., Ltd.; Meidixipuya Pharmaceutical (Shanghai) Co., Ltd.; Ren Feng; Wang Xianlian; Xu Yongmei; Chen Chunlin; Cai Jinna; (28 pag.)CN110194773; (2019); 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. 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C10H9ClN2

N-(trans-2-hydroxycyclohexyl)-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide (224 mg), 1-[4-(chloromethyl)phenyl]-1H-pyrazole (125 mg), tripotassium phosphate trihydrate (330 mg) and Pd(dppf)Cl2 DCM (25.0 mg) were stirred in a mixed solution of 1,4-dioxane (10 mL) and water (1 mL) under a nitrogen atmosphere at 80C for 16 hr. To the reaction mixture was added ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (49.0 mg).

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; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 57999-06-1, 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. 57999-06-1, name is 4-Phenyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of aminoazole 1f-i (1 mmol), acetoacetamides 2a-c (1 mmol), and aromatic aldehyde 3b-f (1 mmol) in 10 mL of ethanol was ultrasonicated at room temperature for 90 min in a round-bottom flask equipped with condenser. The reaction mixture was allowed to stand up to 12 h at room temperature and then was filtered to give the solid compounds 8a-i, which were washed with ethanol and air dried. Reaction products were obtained in high purity and did not require further purification by recrystallization.

The synthetic route of 4-Phenyl-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Muravyova, Elena A.; Desenko, Sergey M.; Rudenko, Roman V.; Shishkina, Svetlana V.; Shishkin, Oleg V.; Sen’ko, Yulia V.; Vashchenko, Elena V.; Chebanov, Valentin A.; Tetrahedron; vol. 67; 48; (2011); p. 9389 – 9400;,
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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 1H-Pyrazole-4-carbonitrile

To a solution of 2-chloro-/V-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide (15.0 g, 38.8 mmol) in acetonitrile (450 mL) were added 1 /-/-pyrazole-4-carbonitrile (5.41 g, 93.1 mmol) and powdered potassium carbonate (16.1 g, 1 16 mmol) and it was stirred overnight at 100C. The reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate and water. Pure title compound precipitated and was filtered off (9.09 g 20.5 mmol, 53 % yield, 97 % purity), The organic phase was washed with brine and dried over sodium sulfate. Concentration in vacuo led to further crude title compound (9.1 1 g., app. 60 % purity). (0390) LC-MS (Method B): Rt = 1 .17 min; MS (ESIneg): m/z = 442 [M-H]” (0391) 1H-NMR (400MHz, DMSO-d6) delta [ppm]: 3.53 (s, 3H), 3.64 (s, 3H), 4.08 (s, 2H), 6.20 (d, 1 H), 6.29 (dd, 1 H), 7.07 (d, 1 H), 7.89 (d, 1 H), 8.12 (br s, 1 H), 8.30 (br s, 1 H), 8.41 – 8.54 (m, 2H), 9.17 (br s, 1 H).

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; HAUFF, Peter; WERNER, Stefan; (94 pag.)WO2019/81573; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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. Quality Control of 1H-Pyrazole-4-carbonitrile

Prepared according General Procedure E, Step 2 from compound Cll (60 mg, 0.14 mmol) and lH-pyrazole-4-carbonitrile (63 mg, 0.67 mmol), with purification by column chromatography on silica gel to provide compound 27 as an off-white solid (27.3 mg, 44%): mp 176-178 C; 1HNMR (300 MHz, CDCI3) delta 7.83 (d, J = 12.3 Hz, 2H), 4.95 (q, J = 18.3 Hz, 2H), 3.53 (d, J = 9.0 Hz, IH), 3.33 (s, 3H), 3.22 (d, J = 9.0 Hz, IH), 2.59 (t, J = 9.3 Hz, IH), 2.26-1.35 (m, 17H), 1.31-1.08 (m, 9H), 0.66 (s, 3H) ppm; ESI MS m/z 437 [M+H-H2Of .

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, Gerald; HERR, Robert, Jason; KARGBO, Robert, Borbo; WO2015/27227; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics