Category: pyrazoles-derivatives

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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Safety of 1H-Pyrazole-4-carbonitrile

To a suspension of 1H-pyrazole-4-carbonitrile (50.5 mg, 0.542 mmol), K3P04(233 mg, 1.084 mmol) and 6-(3-chloro-2-fluoro-6-iodophenyl)pyrimidin-4-ol (190 mg,0.542 mmol) in dioxane (0.24 mL) was added (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (38.6 mg, 0.271 mmol). The vial was then purged with Ar, Cul (5.16 mg, 0.027mmol) was added, and the vial was sealed. The reaction mixture was heated at 80 C.After 16 h, the reaction was cooled to rt, filtered, and the filtrate was concentrated. Purification by reverse phase chromatography gave 1 -(4-chloro-3 -fluoro-2-(6-hydroxypyrimidin-4-yl)phenyl)- 1 H-pyrazole-4-carbonitrile (74 mg, 43% yield) as an offwhite solid. MS(ESI)m/z: 316.3 (M+H). ?H NMR (400MHz, CD3OD) oe 8.54 (s, 1H),8.09 (d, J=0.9 Hz, 1H), 7.97 (s, 1H), 7.80 (dd, J=8.7, 7.8 Hz, 1H), 7.50 (dd, J=8.7, 1.7 Hz, 1H), 6.51 (t,J1.1 Hz, 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; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrazole – Wikipedia,
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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 179692-08-1 as follows. name: Ethyl 4-iodo-1H-pyrazole-5-carboxylate

General procedure: Aryl Halide, tetrakis (triphenylphosphine)palladium or Palladium (II)bis(triphenylphosphine) dichloride (0.05eq) and boronic acid or pinnacol ester (1.2eq) were weighed out into a microwave vessel or sealed tube. Acetonitrile (3mL/mmol) and a 1M aqueous solution of Sodium Carbonate (3eq) were added. The vessel was capped and heated thermally 3-18hrs at 100C. Upon completion, the reaction was cooled and crude product was either triterated via addition of water and collection by filtration or extracted with sat ammonium chloride and DCM. If the crude product was an intermediate, it was taken into the next step in most cases w/o further purification or alternatively submitted for reverse phase HPLC purification when it was a final product.Similar to the procedure as described in General Procedure M, ethyl 4-iodo-lH- pyrazole-3-carboxylate was reacted with 1 -ethyl- lH-pyrazol-4-ylboronic acid to give the title compound (343 mg, 27%) as a yellow oil. LC-MS (ES, m/z): 235 [M+H]+.

According to the analysis of related databases, 179692-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 88095-61-8,Some common heterocyclic compound, 88095-61-8, name is 1-Benzyl-4-nitro-1H-pyrazole, molecular formula is C10H9N3O2, 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 8 mL glass vial equipped with a magnetic stirbar were sequentially added K2CO3 (207 mg, 1.5 mmol), the nitroazole substrate (0.50 mmol), aryl halide (0.50 mmol oras indicated), toluene (0.50 M or 1.0 M), Pd(OAc)2 (5.60mg, 0.025 mmol) and [PCy3H]BF4 (18.4 mg, 0.050 mmol).The reaction mixture was purged with nitrogen through aTeflon-lined cap. Then the cap was replaced with a newTeflon-lined solid cap. The reaction vial was moved to a preheatedreaction block. After stirring for 18 h at the indicatedtemperature, the reaction mixture was cooled to 25 C and concentrated. The residue was purified by flash column chromatography to provide the desired arylated product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Benzyl-4-nitro-1H-pyrazole, its application will become more common.

Reference:
Article; Jung, Haeun; Bae, Seri; Jang, Ha-Lim; Joo, Jung Min; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3009 – 3014;,
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. 1226781-82-3, name is tert-Butyl 2-(methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C11H17N3O4S

3a(2.1g, 7.3mmol) dissolved in dichloromethane (25 ml) in, at 0 C added to trifluoroacetic acid (5 ml), the reaction of the 0 C under 2 hours. The reaction the fluid turns on lathe stem, plus ammonia water (2 ml) quenching the reaction, silica gel column chromatography for purification (dichloromethane/methanol (v/v)=50:1), to obtain white solid3b(1.1g, 80.5% yield).

According to the analysis of related databases, 1226781-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LI, CAI-HU; WEI, YONG-GANG; (99 pag.)TW2017/8222; (2017); A;,
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. 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1-Methyl-1H-pyrazole-4-sulfonyl chloride

Add triethylamine (3.403 mL, 24.414 mmol) to a stirring solution of {2-[4-(2- chloro-pyridin-3-yl)-piperazin-l-yl]-ethyl}-methyl-amine hydrochloride salt (2.000 g, 6.103 mmol) in dichloromethane (100 mL). Add 1 -methyl- lH-pyrazole-4-sulfonyl chloride (1.102 g, 6.103 mmol) at room temperature. Stir at room temperature for 30 min. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate phases and extract the aqueous phase with dichloromethane. Combine the organic phases, dry over sodium sulfate, filter, and concentrate. Purify the resulting material by silica gel chromatography eluting with hexanes: acetone 1 : 1 to afford the title preparation (1.600 g, 66% yield). MS ES: m/z = 399 [M+H]+.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2009/29439; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31230-17-8, The chemical industry reduces the impact on the environment during synthesis 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life.

Method 22; 2-Chloro-5-methyl-N-f5-methyl-lH-pyrazol-3-yl)pyrimidin-4-amine; To a solution of 2,4-dichloro-5-methylpyrimidine (1.25 g, 7.8 mmol) in EtOH (30 ml) was added 5 -methyl- leta-pyrazol-3-ylamine (756 mg, 7.8 mmol) and DIPEA (2.8 mL). The mixture was heated at 70 °C overnight. LC/MS showed the completion of the reaction. The title compound was obtained by filtration under vacuum as a white solid (700 mg). m/z 224.

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-Methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/49041; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 637336-53-9, 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. 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of A-2 (600 mg, 2.34 mmol) in DMF (10ml) was added EDCI (672 mg, 3.51 mmol) and HOBt (538 mg, 3.51 mmol) at 25C. Stirring was continued for 10 min. 4- Amino-l-methyl-lH-pyrazole-3-carboxylic acid methyl ester (362 mg, 2.35 mmol) and triethylamine (0.8 ml, 5.35 mmol) were subsequently added to the above solution. The reaction mixture was stirred at 25C overnight, then quenched with water (8 ml), and extracted with CH2C12. The combined organic layers were washed with brine, dried (Na2S04), filtered, and evaporated. The crude product thus obtained was purified by column chromatography over silica gel (2% MeOH/CH2Cl2) to provide the title compound (642 mg, 69%) as yellow sticky solid.

The synthetic route of Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); 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. 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7F3N2O2

To a solution of 4-{4-[5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl]thiazol-2-yl}piperazine-2-carboxylic acid methyl ester hydrochloride (0.5 g, 1.0 mmol) in 4 ml of N,Ndimethylformamide were added at 0C sequentially ethyl(diisopropyl)amine (0.3 g, 2.5 mmol), (5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetic acid (0.2 g, 1.1 mmol) and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.5 g, 1 .1 mmol). The reaction mixture was stirred for 16 h at room temperature, then poured on waterand extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate and evaporated. The residue is purified by column chromatography on silica gel (cyclohexane / ethyl acetate 4:1) to give 4-{4-[5-(2,6-difluoro-phenyl)-4,5-dihydro-isoxazol-3-yl]thiazol-2-yl}-1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetyl]piperazine-2-carboxylic acid methyl ester (compound I.az.038)as light yellow foam. 1H-NMR (400 MHz, CDCl3): delta = 2.31 (s, 3H), 3.12(t, 1H), 3.34 (dd, 1H), 3.53 (dd, 1H), 3.64 – 3.76 (m, 4H), 3.89 (dd, 1H), 4.20 (dt, 1H), 4.44 (dd, 1H), 4.97 (dd, 1H), 5.22 (dd, 1H), 6.02 (t, 1H), 6.33 (d, 1H), 6.91 (t, 2H), 7.02 (s, 1H), 7.29 (q, 1H). MS:m/z = 599 (M+1).

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 345637-71-0.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; LAMBERTH, Clemens; SULZER-MOSSE, Sarah; CEDERBAUM, Fredrik; UMARYE, Jayant; SONAWANE, Ravindra; WO2013/127784; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 26621-44-3, A common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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: Added to the reaction bottle 3-nitro -1H-pyrazole (5mmol), NBS (5.5mmol), adding 20mLDMF (N, N-dimethyl formamide), then heating to 90 C, under the protection of nitrogen reaction sleepovers. After the reaction is complete, most of the DMF is removed by reduced pressure distillation, solid precipitating a large amount of water, filtering, 20 ml water washing, to obtain the target product solid after drying, light yellow solid. (Yield 87%)

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Yang, Shengyong; Wei, Yuquan; (24 pag.)CN105669558; (2016); A;,
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. 2458-26-6, name is 3-Phenyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8N2

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

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 2458-26-6.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics