Category: pyrazoles-derivatives

The chemical industry reduces the impact on the environment during synthesis 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, I believe this compound will play a more active role in future production and life. 51516-67-7

General procedure: A mixture of theintermediate compounds 2 (1 mmol) and 3 (1 mmol) in ethanol(10 mL) was stirred at reflux for 2 h. After cooling to roomtemperature, the precipitated solid was filtered, and thenrecrystallized from ethanol to give the title compounds 5a-5p.

The chemical industry reduces the impact on the environment during synthesis 51516-67-7. I believe this compound will play a more active role in future production and life.

118430-74-3, 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. 118430-74-3 name is 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine, 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.

A mixture of ferf-butyl 2-(2-(5-bromo-3′-(((tert-butoxycarbonyl)amino)methyl)-5′-fluoro- [1 ,1 ‘-biphenyl]-3-ylcarboxamido)phenyl)acetate (Example 11-B) (100 mg, 0.163 mmol), 3- cyclopropyl-1 -methyl-1 H-pyrazol-5-amine (CAS 118430-74-3) (44.7 mg, 0.326 mmol), Cs2C03 (159 mg, 0.489 mmol) and BrettPhos palladacycle (CAS 1 148148-01-9) (6.51 mg, 8.15 pmol) in CH3CN (2 mL) was heated in a microwave at 160 C for 60 min. The mixture was diluted with EtOAc and water, acidified with 1 N HCI to pH 5. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were concentrated and the residue was purified by HPLC (Method B) to provide the title compound. MS (ESI+) m/z 670.8 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine, and friends who are interested can also refer to it.

5334-39-4, 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. 5334-39-4 name is 3-Methyl-4-nitro-1H-pyrazole, 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.

5.00 g (39.4 mmol) 3-methyl-4-nitro-1 H-pyrazole was dissolved in 115 mL acetonitrile and 9.26 g (47.2 mmol) 4-(bromomethyl)-benzonitrile and 15.4 g (47.2 mmol) cesium carbonate were added. The suspension was stirred at 60 C for 3 h. Afterwards the reaction mixture was filtered, and the filter cake was washed with ethyl acetate. The filtrate was evaporated to dryness and the residue was purified via a Biotage chromatography system (100g snap KP-Sil column, hexane / 40 – 100% ethyl acetate) to give 7.27 g (76%) of the desired title compounds as a mixture. 1H-NMR (400 MHz, DMSO d6) delta (ppm) = 2.39 / 2.59 (s, 3H), 5.42 / 5.55 (s, 2H), 7.35 / 7.47 (d, 2H), 7.80 – 7.85 (m, 2H), 8.29 / 8.99 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-4-nitro-1H-pyrazole, and friends who are interested can also refer to it.

These common heterocyclic compound, 35691-93-1, name is Ethyl 3,5-dimethyl-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. 35691-93-1

EXAMPLE 20; 2-((S)-1-(3-Fluoro-phenyl)-3-{5-[3,5-dimethyl-1-(6-trifluoromethyl-pyridazin-3-yl)-1H-pyrazole-4-carbonyl]-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl}-propylcarbamoyl)-cyclopentanecarboxylic acid (II-1); Step 1-; To a solution of 3,5-dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.2 g, 1.19 mmol) in DMF (10 mL) cooled to 0 C. was added sequentially NaH (60% in mineral oil, 72 mg, 1.78 mmol) and 3-chloro-6-trifluoromethyl-pyridazine (0.22 g, 1.21 mmol; Tetrahedron 1999 55:15067-15070). The resulting mixture was stirred at RT for 3 h then partitioned between EtOAc and saturated aqueous NH4CI. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified via SiO2 chromatography eluting with hexane/EtOAc to afford 0.228 g (62%) of 92a.

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 35691-93-1.

37622-90-5, Adding a certain compound to certain chemical reactions, such as: 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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 37622-90-5.

Ethyl 1H-pyrazole-4-carboxylate (35.0 g, 250 mmol)And K2CO3 (69.0g, 500mmol)In a mixture of CH3CN (250 mL), BnBr (42.7 g, 250 mmol) was added.The mixture was stirred at room temperature for 18 hours and concentrated.The residue was suspended in EA (500 mL), washed with water (200 mL x 2), dried over Na2SO4, and concentrated.The target product (53.0 g, 91.2%) was obtained as a white solid.

According to the analysis of related databases, 37622-90-5, the application of this compound in the production field has become more and more popular.

The chemical industry reduces the impact on the environment during synthesis 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life. 1904-31-0

2-Bromopyridine (1) (1 .Og, 6.3mmol), 1-methyl-i H-pyrazol-3-amine (2) (0.79g,8.2mmol), Xantphos (0.37g, 0.63mmol), and 052003 (4.lg, 12.6mmol) were combined in dry 1,4-dioxane (l5mL). The reaction mixture was then degassed with N2(g), and placed under vacuum for 10mm. Pd2(dba)3 (0.29g, 0.31 mmol) was added and the resulting reaction mixture was heated at 90¡ãC for 30h. It was then pouredonto demineralized water (200mL), and extracted with EtOAc (3 x lOOmL). The organic phases were combined, dried over Na2504, filtered and subsequently concentrated in vacuo. The resulting residue was purified by flash chromatography with EtOAc/Hexane (1:1) to provide N-(i -methyl-i H-pyrazol-3-yl)pyridin-2-am me (3) as a yellow solid (0.75g, 68percent).LCMS (ES): Found i75.2 [M+H].

The chemical industry reduces the impact on the environment during synthesis 1904-31-0. I believe this compound will play a more active role in future production and life.

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. 131797-35-8 name is 5-Chloro-3-(trifluoromethyl)-1H-pyrazole, 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. 131797-35-8

Step 5: 6J-Dichloro-2-[[5-chloro-3-(trifluoromethyl)-lH-pyrazol-l-yllmethyll-4H-pyrido[l,2- alpyrimidin-4-one To a solution of 6,7-dichloro-2-(chloromethyl)-4H-pyrido[l,2-a]pyrimidin-4-one (1 g, 3.80 mmol) in acetonitrile (50 mL) was added 5-chloro-3-(trifluoromethyl)-lH-pyrazole (519 mg, 3.04 mmol), potassium iodide (317 mg, 1.91 mmol) and potassium carbonate (1.05 g, 7.60 mmol). The reaction was stirred for 1 h at 80C. Then the resulting mixture was concentrated in vacuo. The residue was purified by chromatography with ethyl acetate/petroleum ether (1/9) to afford 6,7-dichloro-2-[[5-chloro-3-(trifluoromethyl)-lH-pyrazol- 1- yl]methyl]-4H-pyrido[l,2-a]pyrimidin-4-one (600 mg, 40%) as yellow oil. LCMS (ESI): M+H+ = 397.1 ; HNMR (300 MHz, CDC13) delta 7.60 (d, J = 4.8 Hz, 1H), 7.34 (d, J = 4.8 Hz, 1H), 6.60 (s, 1H), 5.85 (s, 1H), 5.31 (s, 2H).

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

27069-17-6, Name is 3-(4-Methoxyphenyl)-1H-pyrazole, 27069-17-6, 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.

PREPARATION OF EXAMPLE 17 1-(4-Benzoylpiperazin-1-yl)-2-(4-(3-(4-methoxyphenyl)-1H-pyrazol-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)ethane-1,2-dione (Compound 25) EAXMAPLE 17 In a sealed tube dicarbonyl intermediate 10 (50 mg, 0.13 mmol), 3-(4-methoxyphenyl)-1H-pyrazole (105 mg, 0.60 mmol) and 1,4-dioxane (2.5 mL) were combined and heated at 170 C. with microwaves for 20 min. The reaction was concentrated and triturated with MeOH (3 mL). The resulting solids were washed with MeOH and with Et2O to yield 25 (43 mg, 0.08 mmol, 61%) as a tan solid. 1H NMR: (500 MHz, DMSO-d6) delta 12.41 (br s, 1H), 8.91 (d, J=2.8 Hz, 1H), 8.89 (s, 1H), 8.55 (br d, J=3.4 Hz, 1H), 8.20 (d, J=8.7 Hz, 2H), 7.51-7.39 (m, 5H), 7.23 (d, J=2.8 Hz, 1H), 7.08 (d, J=8.7 Hz, 2H), 3.85 (s, 3H), 3.92-3.21 (m, 8H); LC/MS: (ES+) m/z (M+H)+=535; HPLC Rt=1.40 min., column Q, conditions B.

Statistics shows that 3-(4-Methoxyphenyl)-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 27069-17-6.

1280210-79-8, 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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (250 mg, 1.2 mmol) in DMF (5 mL) was added NaH (96 mg, 2.4 mmol (60% in mineral oil)), with the reaction mixture being cooled with an ice bath. The resulting mixture was stirred at room temperature for 1 h, whereupon iodoethane (374 mg, 2.4 mmol) was added, and the resulting reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with water (10 mL) and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (10 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo to give 135 and 135-A as a crude product. MS 238.2 [M + H]+. (0141) [0090] Synthesis of 136 and 136- A. To a solution of 135 and 135-A (1.2 mmol, crude product from last step) in DCM (6 mL) was added TFA (2 mL) dropwise while the reaction mixture was cooled with an ice bath. The reaction mixture was stirred at room temperature 1 h, whereupon the solvent was removed in vacuo to give 136 and 136-A as a crude product which was used in the next step without further purification. MS 138.2 [M + H]+. (0142) [0091] Synthesis of 137. A mixture of 136 and 136-A (1.2 mmol, crude product from last step) and A3 (491 mg, 1.0 mmol) in DMSO (10 mL) was stirred at room temperature for 10 min, then Na2C03 (848 mg, 8.0 mol) was added, and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with water (20 mL) and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine (20 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 50 : 1) to give a crude product which was a mixture of the regioisomers 137 and 137-A. The crude product was further purified by Prep-TLC (DCM : MeOH = 30 : 1) to give 137 (150 mg, 36%) as a yellow solid. MS 415.1 [M + H]+.

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.

143426-52-2, The chemical industry reduces the impact on the environment during synthesis 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A mixture of methyl 2-fluoro-3,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.51 g), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (0.48 g), tetrakis(triphenylphosphine)palladium(0) (0.096 g), 2 M aqueous sodium carbonate solution (1.7 mL), and DME (17 mL) was stirred under a nitrogen atmosphere at 90C for 15 hr. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.35 g). MS: [M+H]+ 339.1

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