Category: pyrazoles-derivatives

Application of 214614-81-0,Some common heterocyclic compound, 214614-81-0, name is 4-Bromo-1-(2-hydroxyethyl)pyrazole, molecular formula is C5H7BrN2O, 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 22b (0.45g, 2.36mmol) and bis(pinacolato)diboron (0.718g, 2.83mmol) in DMF (2OmL), was added KOAc (0.694g, 7.08mmol). The mixture was 0 degassed with N2, stirred for 1 Omin and added Pd(dppf)Cl2 (58mg, 0.071 mmol). The mixture was degassed with N2 and stirred at 8O0C overnight. DMF was removed and the residue was purified by column chromatography (EA:PE=1 :10) to afford of 22c (149mg, 26.6% yield).

The synthetic route of 214614-81-0 has been constantly updated, and we look forward to future research findings.

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. 179057-10-4, name is Methyl 4-(1H-pyrazol-5-yl)benzoate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 179057-10-4

Example 168: 1-(4-Benzoyl-2-methyl-piperazin-1-V-)-2-r4-(2H-pyraz?l-3- yl)-phen yli-etha?e-1.2-dio?e; To a solution of 4-(2/-/-pyrazol-3-yl)-benzoic acid methyl ether (0.2 g, 1 mmol) and (4-benzoyl-2-methyl-piperazin-1-yl)-acetonitrile (0.24 g, 1 mmol) in anhydrous THF (2 mL) was added by drops 1.06 M solution LiHMDS in THF (4 mL, 4 mmol). The reaction mixture was stirred for 1 hour, and m-CPBA was added (0.67 g, 4 mmol). The mixture was stirred for 1 hour additionally, quenched with water, extracted with EtOAc, dried over sodium sulfate, filtered and evaporated. The residue was purified by SiO2 chromatography using 10% MeOH/ethyl acetate as eluent to obtain 1-(4-benzoyl-2-methyl-piperazin-1-yl)- 2-[4-(2H-pyrazol-3-yl)-phenyl]-ethane-1,2-dione (0.09 g, 22%). LCMS: CaICd for C23H22N4O3 ? H+: m/z = 403.5. Found: m/z = 403, 404. 1H NMR (DMSO- d6): 13.59 and 13.16 (two br s, 1H, NH-pyrazole); 8.06 (m, 2H); 7.95-7.86 (m, 3H); 7.45-7.40 (m, 5H); 6.89 (br s, 1 H); 4.68-4.30 (br signal, 2 H); 3.29-3.43 (br signal, 2H); 3.16 (m, 1H); 3.08-2.85 (br signal, 2H); 1.20 (br signal,.3H).

The synthetic route of 179057-10-4 has been constantly updated, and we look forward to future research findings.

Reference of 176969-34-9,Some common heterocyclic compound, 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H6F2N2O2, 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 7: Production of N-[2-[3-chloro-5-(cyclopropylethynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide To a 1 ml solution of 68 mg of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid in dichloromethane, 10 mg of N,N-dimethylformamide and 66 mg of oxalyl chloride were added. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was dissolved in 1 ml of dichloromethane and, with stirring under cooling with ice, added dropwisely to a mixed solution of 100 mg of 2-amino-1-[3-chloro-5-(cyclopropylethynyl)pyridin-2-yl]ethanone-O-isopropyl oxime and 200 mg of potassium carbonate in 2 ml of dichloromethane and 2 ml of water. After completion of the dropwise addition, stirring was further continued for 1 hour at room temperature. After completion of the reaction, 10 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (10 ml*1). The obtained organic layer was washed with water (10 ml*1), and then dehydrated and dried by using saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography by eluting it with ethyl acetate-hexane (2:3), to obtain 150 mg of the desired product as a pale yellow resinous substance (E/Z=2/1). 1H NMR (CDCl3, Me4Si, 300 MHz) b 8.45 and 8.43 (d, J=1.8 Hz, 1H), 7.88 and 7.82 (s, 1H), 7.68 and 7.66 (d, J=1.8 Hz, 1H), 7.12 (bs, 1H), 6.85 and 6.75 (t, J=54.2 Hz, 1H), 4.70 and 4.46 (d, J=6.1, 4.9 Hz, 2H), 4.47 and 4.36 (sep, J=6.3 Hz, 1H), 3.90 and 3.87 (s, 3H), 1.4-1.55 (m, 1H), 1.32 and 1.18 (d, J=6.3 Hz, 6H), 0.8-1.0 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, its application will become more common.

Reference of 133228-21-4, The chemical industry reduces the impact on the environment during synthesis 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide, I believe this compound will play a more active role in future production and life.

To a solution of N,N-dimethylsulfamoylpyrazole (44.0 g, 0.251 mol) in dry tetrahydrofuran (500 ml) at -78C was added dropwise a solution of n-butyllithium (2.5 M in hexane, 105.5 ml, 0.264 mol) while maintaining the temperature below -60C. A thick solid formed during the addition. Upon completion of the addition the reaction mixture was maintained for an additional 15 minutes, after which time a solution of 1,2-dibromotetrachloroethane (90 g, 0.276 mol) in tetrahydrofuran (150 ml) was added dropwise while maintaining the temperature below -70C. The reaction mixture turned a clear orange; stirring was continued for an additional 15 minutes. The -78C bath was removed and the reaction was quenched with water (600 ml). The reaction mixture was extracted with methylene chloride (4x), and the organic extracts were dried over magnesium sulfate and concentrated. The crude product was further purified by chromatography on silica gel using methylene chloride-hexane (50 : 50) as eluent to afford 57.04 g of the title product as clear colorless oil. 1H NMR (CDCl3): delta 3.07 (d, 6H), 6.44 (m, 1H), 7.62 (m, 1H).

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, N,N-Dimethyl-1H-pyrazole-1-sulfonamide, other downstream synthetic routes, hurry up and to see.

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 25699-83-6 as follows. Product Details of 25699-83-6

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (15 mL). This was followed by dropwise addition of a 4-(1H-pyrazol-1-yl)benzonitrile (250 mg, 1.48 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) with stirring at 0 C. To this was added LiAlH4 (337 mg, 8.87 mmol, 6.00 equiv). The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of NaOH (15%, aq). The resulting solution was extracted with 3*50 mL of dichloromethane and the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under vacuum. The product was obtained as 0.251 mg of a white crude solid.

According to the analysis of related databases, 25699-83-6, the application of this compound in the production field has become more and more popular.

Some common heterocyclic compound, 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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. SDS of cas: 3994-50-1

Pd / C (10%, 500 mg) was added to the column1-methyl-4-nitro-1H-pyrazole (1.90 g, 14.9 mmol)And methanol (25 mL)Hydrogen at room temperature overnight.Diatomaceous earth filter, dichloromethane washing filter cake,The filtrate was concentrated under reduced pressure, (Eluent: ethyl acetate / methanol (v / v) = 18/1) to give 1.35 g of a black solid, yield:83.7%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3994-50-1, its application will become more common.

These common heterocyclic compound, 103626-03-5, name is Ethyl 1-methyl-3-oxo-2,3-dihydro-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. name: Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate

Example 264 A mixture of ethyl 3-hydroxy-1-methyl-1H-pyrazole-4-carboxylate (1.93 g), 4-(4-chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole (3.89 g), potassium carbonate (3.15 g) and N,N-dimethylformamide (30 mL) was stirred overnight at 60C. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained colorless crystals were collected by filtration to give ethyl 3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxylate (5.23 g, yield 97%). The crystals were recrystallized from acetone-hexane. melting point: 134-135C.

The synthetic route of Ethyl 1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 3994-50-1, name is 1-Methyl-4-nitro-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. Recommanded Product: 3994-50-1

To a solution of tert-butyl N- [(15)-i -(5 -bromopyridin-3 -yl)but-3 -en- l-yl]carbamate (1.0 g, 3.06 mmol), prepared as described in Intermediate 26, in dioxane (10ml) was added 1-methyl-4-nitro-1H-pyrazole (0.427 g, 3.36 mmol), di(adamantan-1-yl)(butyl)phosphine (0.164 g, 0.458 mmol), K2C03 (1.267 g, 9.17 mmol) and pivalic acid(0.106 ml, 0.917 mmol). The reaction mixture was purged with Ar. Pd(OAc)2 (0.069 g,0.306 mmol) was added and the solution was stirred at 100 C. After 4 h, the reactionwas quenched with water (20 ml) and extracted with EtOAc (3 x 50 ml). The combinedorganic layers were washed with brine (20 ml), dried (MgSO4), filtered, and concentrated.The residue was purified by normal phase chromatography using heptanes and EtOAc aseluents to give tert-butyl N-[( 15)-i -[5 -(1 -methyl-4-nitro- 1 H-pyrazol-5 -yl)pyridin-3 -yl]but-3-en-i-yl]carbamate (0.85 g, 74%) as a white foam. MS(ESI) m/z: 374.5 (M+H).?H NMR (500MHz, CDC13) oe 8.74 (d, J=i .9 Hz, 1H), 8.57 (d, J=i .9 Hz, 1H), 8.25 (s,1H), 7.72 (t, J=i.9 Hz, 1H), 5.73 (ddt, J=17.i, 10.2, 7.2 Hz, 1H), 5.26 – 5.17 (m, 2H),4.99 (br. s., 1H), 4.93 – 4.84 (m, 1H), 3.80 (s, 3H), 2.75 – 2.52 (m, 2H), 1.43 (br. s., 9H).

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

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 34605-66-8 as follows. Recommanded Product: 34605-66-8

To a solution of 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole (6.4 g) in tetrahydrofuran (70 mL) was added dropwise n-butyllithium (1.6 M hexane solution, 27 mL) at -78 C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added dropwise di-tert-butyl dicarbonate (11 mL) at -78 C., and the mixture was stirred for 2 hr while gradually raising the temperature to room temperature. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (7.9 g). 1H NMR (400 MHz, DMSO-d6) delta1.56 (9H, s), 1.94-2.13 (6H, m), 4.09 (3H, s), 5.77 (2H, s), 6.84 (1H, s). MS(ESI+): [M+H]+ 276.1.

According to the analysis of related databases, 34605-66-8, the application of this compound in the production field has become more and more popular.

Adding a certain compound to certain chemical reactions, such as: 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, 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 52222-73-8, Computed Properties of C4H3F3N2

Example 29 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-4-[4-(trifluoromethyl)-1H-pyrazol-1-yl]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one Under argon atmosphere, 200 mg (purity 62%, 0.24 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 15A) was suspended in 2.5 ml of absolute acetonitrile, and 656 mg (4.82 mmol) of 4-(trifluoromethyl)-1H-pyrazole, 157 mg (0.48 mmol) of caesium carbonate, 7 mg (0.05 mmol) of copper(I) oxide and 26 mg (0.19 mmol) of 2-hydroxybenzaldehyde-oxime were added. The mixture was heated in the microwave for 1 h at 200 C. The reaction solution was filtered and purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80?100:0). 85 mg (63% of theor.) of the target compound was obtained. LC-MS (method 1): Rt=1.33 min; MS (ESIpos): m/z=523 [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.56 (s, 6H), 5.91 (s, 2H), 7.15 (t, 1H), 7.20-7.25 (m, 2H), 7.34-7.39 (m, 1H), 7.52 (dd, 1H), 8.51 (s, 1H), 8.71 (dd, 1H), 8.92 (dd, 1H), 9.30 (s, 1H), 11.99 (s, 1H).

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