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. 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 27006-76-4

General procedure: To a well stirred solution of substituted phenol (30 mmol) in DMF or DMSO (30 mL), KOH wasadded (40 mmol) at room temperature. The resulting mixture was heated to 40 C for 2-4 h, and thencompound 1 (20 mmol) was added thereto. The reaction solution was heated to 105 C for 8-24 h.After being cooled to room temperature, the mixture was poured into water and extracted with ethylacetate (3 50 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered,and evaporated to afford intermediate 2, with yields ranging from 52% to 76% [25].

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; Dai, Hong; Yao, Wei; Fang, Yuan; Sun, Siyu; Shi, Yujun; Chen, Jia; Jiang, Guoqing; Shi, Jian; Molecules; vol. 22; 12; (2017);,
Pyrazole – Wikipedia,
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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. 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C5H5F3N2

Example 32 Synthesis of l-[l-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[5-methyl-3- (trifluoromethyl)pyrazol-l-yl]pyrrolidin-2-one step d [0182] a) A mixture of l-(4-fluorophenyl)-5-isopropylpyrazol-4-amine (1.0 g, 4.54 mmol), 3-bromotetrahydrofuran-2-one (0.462 mL, 5.0 mmol) and AlMe3 (3.4 mL, 6.8 mmol, 2 M in toluene) in DCE (50 mL) was stirred for 2 hrs at rt followed by 45 min at 50 C. The mixture was then cooled to room temperature, quenched with IN HC1 (50 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (Si02, 0 ~ 100% EtOAc/CH2Cl2 gradient elution) to give 2-bromo-N-[l-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-4-hydroxy- butanamide (1.38 g, 79%). [0183] b) A mixture of 2-bromo-N-[l-(4-fluorophenyl)-5-isopropyl-pyrazol-4-yl]-4- hydroxy-butanamide (1.38 g, 3.59 mmol), methanesulfonyl chloride (0.36 mL, 4.65 mmol) and NEt3 (0.75 mL, 5.35 mmol) in CH2C12 (50 mL) was stirred at 0 C for 40 min. The mixture was then quenched with water (50 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the desired mesylate (1.65 g, 99%). [0184] c) A mixture of the above mesylate (0.350 g, 0.75 mmol) was stirred with NaH (0.200 g, 5.0 mmol, 60% in mineral oil) in THF (7 mL) at 50 C for 30 min. It was then cooled to rt, quenched with saturated aqueous NH4CI (50 mL) and extracted with EtOAc (50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (Si02, 0 ~ 80% EtOAc/CH2Cl2 gradient elution) to give 3- bromo-l-[l-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.160 g, 58%). [0185] d) A mixture of 3-bromo-l-[l-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin- 2-one (0.023 g, 0.063 mmol), 5-methyl-3-(trifluoromethyl)-lH-pyrazole (0.040 g, 0.27 mmol) and K2C03 (0.060 g, 0.43 mmol) in DMF (1 mL) was stirred at 60 C for 1 hr. It was then cooled to room temperature, quenched with water (30 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (Si02, 0 ~ 100% EtOAc/hexanes gradient elution) to give the title compound (0.022 g, 80%). XH NMR (400 MHz, CDC13) delta 7.52 (s, 1 H), 7.37 (dd, J= 9.2, 4.8 Hz, 2 H), 7.17 (dd, J= 8.6, 8.6 Hz, 2 H), 6.32 (s, 1 H), 5.05 (dd, J= 9.2, 5.6 Hz, 1 H), 4.07 (m, 1 H), 3.80 (m, 1 H), 2.84 – 3.02 (m, 2 H), 2.74 (m, 1 H), 2.45 (s, 3 H), 1.21 (d, J= 7.6 Hz, 3 H), 1.1 1 (d, J= 6.8 Hz, 3 H); MS: (ES) m/z calculated for C2iH21F4 50 [M + H]+ 436.1, found 436.1.

The synthetic route of 10010-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Pingchen; LI, Yandong; POWERS, Jay P.; MALATHONG, Viengkham; PUNNA, Sreenivas; TANAKA, Hiroko; ZHANG, Penglie; WO2014/89495; (2014); 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. 2075-46-9, name is 4-Nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., Safety of 4-Nitro-1H-pyrazole

General procedure: Into a 2 dram vial was placed 5-nitro-8-hydroxyquinonline (63 mg, 0.33 mmol), Ru/PS nanoparticle catalyst (8.0 mg, 0.477 mmol Ru/gram catalyst, 1.2 mol%), and hydrazine monohydrate (42 muL, 2.5 equiv) in 4 ml of THF. The reaction mixture was stirred for 2 hr, at which point the solvent was removed under reduced pressure. The product was extracted from the solid mixture with 3x 2 ml EtOH. The combined ethanol extracts were then passed through a short silica plug in a pipet and the silica plug was washed 2 times with 1 ml ethanol. The EtOH was then removed on a rotary evaporator under reduced pressure. The product 5-(hydroxyamino)quinolin-8-ol was isolated as an orange solid (51 mg, 0.29 mmol, 87% yield). For some of the more complex substrates, the reaction results are highly temperature sensitive, the reactions can be forced to completion by adding extra equivalents of hydrazine, and by raising the temperature to 27 C.

The synthetic route of 2075-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tyler, Jefferson H.; Nazari, S. Hadi; Patterson, Robert H.; Udumula, Venkatareddy; Smith, Stacey J.; Michaelis, David J.; Tetrahedron Letters; vol. 58; 1; (2017); p. 82 – 86;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5334-40-7, 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2. Synthesis of 4-nitro-1H-pyrazole-3-carboxylic acid (trans-4- methoxymethoxy-cvclohexyl)-amideA mixture of 4-nitro-3-pyrazolecarboxylic acid (2.32 g, 14.8 mmol), trans 4- aminocyclohexanol (2.95 g, 18.5 mmol), EDAC (3.55 g, 18.5 mmol) and HOBt (2.50 g, 18.5 mmol) in DMF (75 ml) was stirred at ambient temperature for 16 hours. The mixture was reduced in vacuo, partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic layer was washed (water, brine) dried (MgSO4), and reduced in vacuo to give a yellow oil (3.25 g), which was purified by column chromatography, eluting 0-100 percent EtOAc in petroleum ether, then 1-25 percent MeOH in EtOAc to give 4-nitro-1H-pyrazole-3-carboxylic acid (trans- 4-methoxymethoxy-cyclohexyl)-amide as a pale yellow solid (1.25 g). (LC/MS: Rt 2.11 [M+H]+ 297.25).

The synthetic route of 4-Nitro-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77414; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference 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.

2.08 kg of cesium carbonate,0.78 kg of 4-bromopyrazole was dissolved in 4 liters of N-methylpyrrolidone,Heated to 80 degrees,A 5 liter solution of N-methylpyrrolidone was added to 1.8 kg of compound (CZT-7)Reaction for 12 hours.Cooled to room temperature,Add 50 litersMethyl tert-butyl etherwith50 liters of water,Stir for 1 hour.After dispensing,The organic phase was washed with 20 liters of * 4 water and dried 50%Liter of hexane and stirred at room temperature for 2 hours. Filtered and dried to give 1.35 kg of compound (CZT-8) in a yield of 77%

The synthetic route of 2075-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Aikangrui Pharmaceutical Technology Co., Ltd.; Fan Linfeng; Zhu Yangwei; Xu Zhonghui; Zhang Changxuan; Shi Peng; Qiu Aiyun; (11 pag.)CN106317024; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 2075-45-8,Some common heterocyclic compound, 2075-45-8, name is 4-Bromo-1H-pyrazole, molecular formula is C3H3BrN2, 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.

Step 1. A mixture of 4-bromo-1H-pyrazole (150 g, 1.02 mol, 1.0 eq), 3,4-dihydro-2H-pyran (128 g, 1.50 mol, 1.5 eq) and trifluoroacetic acid (7.8 mL, 0.10 mol, 0.1 eq) was stirred at 80 C. for 16 h. Progress of the reaction was monitored by TLC (10% ethyl acetate-hexane Rf=0.4). After completion of reaction, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and the solvents evaporated under reduced pressure to obtain 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (180 g, 76%) as a brown oil. LCMS purity: 81.4%; (ES+): m/z 231.2 (M+H+); tr=1.88 min.

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

Reference:
Patent; INNOV17 LLC; Gaweco, Anderson; Tilley, Jefferson; Blinn, James; US2015/252051; (2015); 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. 13808-64-5, name is 4-Bromo-3-methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H5BrN2

A mixture of (bromomethyl) benzene (1.3 g, 7.6 mmol) , 4-bromo-3-methyl-1H-pyrazole (1.01 g, 6.27 mmol) and potassium carbonate (2.1 g, 15 mmol) in DMF (15 mL) was stirred at 50 for 6 h. The reaction mixture was diluted with water (30 mL) . The resulting mixture was extracted with EtOAc (30 mL × 3) . The combined organic layers were washed with saturated aqueous NaCl (20 mL) , dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 5/1 to give a light yellow mixture of isomerides (806 mg, 51.2) .[1663]MS (ESI, pos. ion) m/z: 251.10 [M+1]+.

According to the analysis of related databases, 13808-64-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; ZHANG, Yingjun; CHENG, Changchung; HUANG, Jiuzhong; BAI, Shun; REN, Xingye; LI, Zhi; ZHOU, Youbai; (368 pag.)WO2016/615; (2016); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3994-50-1, The chemical industry reduces the impact on the environment during synthesis 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A mixture of a portion (0.7 g) of the material so obtained, platinum oxide (0.05 g), ethyl acetate (5 ml) and ethanol (15 ml) was stirred under 3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material (0.6 g); 1H NMR Spectrum: (DMSOd6) 3.64 (s, 3H), 6.86 (s, IH), 6.97 (s, IH).

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 4522-35-4, The chemical industry reduces the impact on the environment during synthesis 4522-35-4, name is 3-Iodo-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Example 234. Synthesis of 3-fluoro-2-(4-(l-((3R,4R)-4- hydroxytetrahydrofuran-3-yl)-lH-pyrazol-3-yl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4- b]pyridin-2-yl)benzonitrile, 1-234 Synthesis of compound 234.2. To a solution of 234.1 (5.0g, 25.77mmol, 1.0 eq) in THF (15mL) was added LDA (2M in THF ) (14mL, 28.33mmol, 1.1 eq) at -78C. Reaction mixture was stirred at -40 C for lh. To this added solution of 3,6-dioxabicyclo[3.1.0]hexane (1.77g, 20.61mmol, 0.8eq) in THF (lOmL). Reaction mixture was stirred at room temperature for lh and heated at 80 C for 2 4h .Upon completion of the reaction, mixture was transferred into water, and extracted with EtOAc. Organic layers were combined, washed with brin, dried over Na2S04 and concentrated under reduced pressure to pressure to obtain crude which was purified by column chromatography to furnish 234.2 (2.5 g, 34.63%). MS(ES): m/z 281.2 [M+H]+.

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

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; MONDAL, Sayan; (342 pag.)WO2017/40757; (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. 27258-32-8, name is 1-Methyl-1H-pyrazole-3-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 27258-32-8

To (E)-3-(2-((5-methyl-2 H-tetrazol-2-yl)methyl)-4-(trifluoromethyl) phenyl)- 1 -(piperazin- 1- yl)prop-2-en-1-one (Example 88, step 2) (110 mg, 0.289 mmol) in methanol (2.62 1 mL) was added acetic acid (0.262 m L) and 1-methyl-i H-pyrazole-3-carbaldehyde (commerciallyavailable) (47.8 mg, 0.434 mmol) and the mixture was stirred for 5 minutes. 2-Picoline borane (49.0 mg, 0.463 mmol) was added and the mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure. Purification of the crude product by chromatography on silica using a gradient from 0 – 100percent EtOAc in iso-hexane followed by methanol in EtOAc (10percent) afforded the title compound;LC-MS: Rt = 2.i6mins; [M+H] 475.4, Method 8minLowpHvoi.1H NMR (400 MHz, DMSO-d6) O 8.07 (1H, d), 7.85 (1H, 5), 7.80 (1H, d), 7.75 (1H, d), 7.6 (1H, 5), 7.24 (1H, 5), 6.15-6.07 (3H, mult), 3.79 (3H, 5), 3.67-3.50 (4H, mult), 3.48-3.28 (4H, mult), 2.44-2.32 (7H, mult).

The synthetic route of 27258-32-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BEATTIE, David; BAETTIG, Urs; LEGRAND, Darren Mark; LISTER, Andrew Stuart; MCKENNA, Jeffrey; PEARCE, David William; SANDHAM, David Andrew; STEWARD, Oliver Ross; THOMSON, Christopher; WO2015/8230; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics