pyrazoles-derivatives

Adding some certain compound to certain chemical reactions, such as: 5952-92-1, name is 1-Methyl-1H-pyrazole-4-carboxylic acid, 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 5952-92-1. 5952-92-1

A suspension of 1 -methyl- lH-pyrazole-4-carboxy lie acid (0.25 g) in thionyl chloride (4 mL) was stirred at reflux for 30 minutes. The reaction was concentrated, the residue azeotroped with toluene and dissolved in acetonitrile (5 mL). To the cooled (0 ¡ãC) solution, a 2 M solution of (trimethylsilyl)diazomethane in hexanes (1.5 mL) was added and the mixture stirred at 0 ¡ãC for 1 hour. A solution of 33 wt. percent hydrogen bromide in acetic acid (1.0 mL) was added and the mixture stirred at room temperature for a further 80 minutes. To the reaction mixture, tert-butyl methyl ether (20 mL) was added and the resultant precipitate isolated by filtration to give the title product having the following physical properties (0.22 g). LC MS rR 1.23 minutes; MS (ES+) m/z 203 and 205 (M+H) a.

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 1-Methyl-1H-pyrazole-4-carboxylic acid.

35277-02-2, 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. 35277-02-2 name is 4-Fluoro-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.

Intermediate (11): 4-fluoro-1-(4-nitrophenyl)-1H-pyrazole To a solution of 4-fluoro-1H-pyrazole (250 mg, 2.90 mmol) and potassium carbonate (803 mg, 5.81 mmol) in acetonitrile (3 mL) was added 4-fluoronitrobenzene (430 mg, 3.05 mmol). The resulting mixture was stirred at 70 C. for 2 hours. The reaction was then filtered and concentrated. Purification by column chromatography gave 4-fluoro-1-(4-nitrophenyl)-1H-pyrazole (400 mg, 67%). 1H NMR (400 MHz, CDCl3, delta): 8.34 (d, 2H), 7.91 (d, 1H), 7.81 (d, 2H), 7.67 (d, 1H).

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

Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-Nitro-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 2075-46-9, 2075-46-9

The 4-amino-l -methyl- lH-pyrazole used as a starting material was prepared as follows :-Dimethyl sulphate (5 ml) was slowly added to a stirred solution of 4-nitropyrazole (2 g) in IN aqueous sodium hydroxide solution (20 ml) that had been warmed to 30C and the resultant mixture was stirred at that temperature for 48 hours. The mixture was cooled to ambient temperature and the precipitate was isolated, washed with cold water and dried under vacuum. There was thus obtained l-methyl-4-nitro-lH-pyrazole (1.5 g); 1H NMR: (DMSOd6) 3.91 (s, IH), 8.24 (s, IH), 8.85 (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, 4-Nitro-1H-pyrazole, 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 25016-11-9 as follows. 25016-11-9

1-Methyl-1H-pyrazole-4-carbaldehyde (CAS : [25016-11-9 ]) (100 mg, 0.9 mmol) was added dropwise at 20 C, to a solution of intermediate 9 (300 mg, 0.9 mmol) and Et3N (0.23 mL, 1.64 mmol) in MeOH (5 mL). The mixture was stirred at rt for 4 h. The mixture was cooled to 0 C then NaBH4 (47 mg, 1.23 mmol) was added portionwise and the mixture was stirred at rt for 15 h. The mixture was poured into ice water containing NH4Cl 10%, and extracted with DCM three times. The organic layers were gathered, washed with brine, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (Stationary phase: irregular SiOH 15-40mum 24g GRACE, Mobile phase: Gradient from 0.1% NH4OH, 97% DCM, 3% MeOH to 0.1% NH4OH, 95% DCM, 5% MeOH). The fractions containing product were collected and evaporated to dryness yielding 140 mg (yield 40%) of compound 11.

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

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. 5932-27-4 name is Ethyl 1H-pyrazole-3-carboxylate, 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. 5932-27-4

Step 2: Nitrogen protection, 1H-pyrazole-3-carboxylic acid ethyl ester (3.7 g, 26.2 mmol) dissolved in dry DMF(25 mL), 60percent NaH (1.0 g, 26.2 mmol) was added in four portions at 0 ¡ãC. After stirring for 15 min, slowly add 2-(3,5-Dimethyl-1H-pyrazol-1-yl)-6-fluoropyridine (4.0 g, 20.9 mmol), warmed to 110 ¡ã C and stirred overnight.The reaction was quenched by adding an appropriate amount of water and extracted three times with dichloromethane.The combined organics were dried with MgSO4 for 2 h. Filter out MgSO4,The solvent was distilled off, and the crude product was separated by column chromatography (eluent petroleum ether (60-90 ¡ã C) / ethyl acetate, 15:1 by volume) to obtain white powder.Final (5.7 g, yield 88percent).

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

Some common heterocyclic compound, 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. 89501-90-6

To a mixture of 4-(lH-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H- pyrrolo[2,3-d]pyrimidine (prepared as described in WO 2007/070514 Example 65; 0.248 g, 0.785 mmol) in 1,4-dioxane (4 mL)was added 1.0 M of potassium tert-butoxide in tert-butyl alcohol (0.822 mL, 0.822 mmol). The reaction was stirred at RT for 10 min. To the resulting mixture was added benzyl 4-{3-fluoro-2-[(methylsulfonyl)oxy]propyl}piperazine-l- carboxylate (0.280 g, 0.748 mmol). The reaction was stirred at 95 C for 2 h, quenched with aqueous ammonium chloride, and extracted with EtOAc. The combined organic layers were washed with water, brine, dried and evaporated to dryness. The residue was purified on silica gel column, eluting with 0 to 80% EtOAc in hexanes, to provide the desired product and (+/-)- benzyl 4-(2-fluoro-l-{[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin- 4-yl)-lH-pyrazol-l-yl]methyl}ethyl)piperazine-l-carboxylate (128 mg, 28.8%). LCMS calculated for C3oH4iF 703Si(M+H)+: m/z = 594.3; Found: 594.3. A mixture of (+/-)-benzyl 4-{3-fluoro-2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H- pyrrolo[2,3-d]pyrimidin-4-yl)-lH-pyrazol-l-yl]propyl}piperazine-l-carboxylate (0.064 g, 0.11 mmol) and (+/-)-benzyl 4-(2-fluoro-l-{[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H- pyrrolo[2,3-d]pyrimidin-4-yl)-lH-pyrazol-l-yl]methyl}ethyl)piperazine-l-carboxylate (0.064 g, 0.11 mmol) in 5 mL of methanol was hydrogenated in the presence of 5% Pd/C, under balloon pressure of hydrogen, for 2 h. After filtering off the catalyst, the filtrate was concentrated and used directly in next step. LCMS calculated for C22H35F 70Si(M+H)+: m/z = 460.3; Found: 460.4. To a mixture of (+/-)-4-{ l-[2-fluoro-l-(piperazin-l-ylmethyl)ethyl]-lH-pyrazol-4-yl}- 7- {[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (0.050 g, 0.11 mmol) and (+/-)-4- [ 1 -(3 -fluoro-2-piperazin- 1 -ylpropyl)- 1 H-pyrazol-4-yl]-7- { [2- (trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (0.050 g, 0.11 mmol) in acetonitrile (2 mL) was added triethylamine (0.0606 mL, 0.435 mmol) followed by 1-methyl- lH-pyrazole-3-sulfonyl chloride (0.0491 g, 0.272 mmol). The reaction was stirred at RT for 1 h and evaporated to dryness. LCMS calculated for C26H39F 903SSi(M+H)+: m/z = 604.3; Found: 604.4. The crude mixture from above was treated with 2 mL of TFA at RT for 1 h, evaporated to dryness. The residue was dissolved in 3 mL of methanol and treated with 100 muL ethylenediamine at RT for 1 h. The reaction mixture was purified on RP-HPLC (XBridge C-18 Column, eluting with a gradient of acetonitrile/water containing 0.1% TFA to give the desired products as TFA salts. First peak, with retention time 0.844 min at Waters SunFire HPLC column (CI 8, 2.1×50 mm, 5 muMu, injection volume 2 muL, flow rate 3 mL/min, eluting with a gradient from 2 to 80% of acetonitrile/water with 0.025% TFA, was found to be titled compound, LCMS calculated for C2oH25F 902S(M+H)+: m/z = 474.2; Found: 474.1. Second peak with retention time 0.961 min at the same analytical HPLC conditions was isomer (+/-)-4- ( 1 -(3 -fluoro-2-(4-( 1 -methyl- 1 H-pyrazol-3 -ylsulfonyl)piperazin- 1 -yl)propyl)- 1 H-pyrazol-4- yl)-7H-pyrrolo[2,3-d]pyrimidine, LCMS calculated for C2oH25F 902S(M+H)+: m/z = 474.2; Found: 474.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 89501-90-6, its application will become more common.

1453-58-3, 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. 1453-58-3, name is 3-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows.

Sodium hydride (30 mg, 1.25 mmol) was added to a solution of 3-methylpyrazole (88 mg, 1.07 mmol) in dry THF (5 cm3) under an atmosphere of argon. A solution of 7-tert-butyl-2-chloro-1-azaxanthone (280 mg, 0.97 mmol) in dry THF (5 cm3) was then added to the reaction mixture, which was stirred at 65 ¡ãC for 16 h. The reaction mixture was allowed to cool to room temperature before water (~10 cm3) was added to the reaction mixture. The precipitate was collected via centrifugation and the resultant solid triturated with a minimum volume of Et2O. The solvent was decanted to yield the title compound as a white solid (290 mg, 0.87 mmol, 90percent). deltaH (CDCI3, 400 MHz) 1.39 (9H, s, tBu), 2.37 (1H, s, Me), 6.31 (1H, d, J 2.8, H2′), 7.51 (1H, d, J 8.8, H10), 7.80 (1H, dd, J 8.8; 2.8, H9), 7.99 (1H, d, J 8.4, H2), 8.27 (1H, d, J 2.8, H7), 8.51 (1H, d, J 2.8, H 1′, 8.72 (1H, d, J 8.4, H3). deltac (CDCI3, 100 MHz) 14.2 (Me), 31.6 (C14), 35.1 (C13), 109.7 (C2), 110.1 (C2′), 113.9 (C4), 118.1 (C10), 121.4 (C6), 122.7 (C7), 129.0 (C1′), 133.4 (C9), 140.1 (C3), 148.3 (C8), 153.7 (C11), 153.9 (C12), 154.0 (C3′), 160.0 (C1), 177.0 (C5). m/z (ES+) 688.9 (100percent, 2M + H), 334.3 (50percent, M + H). HRMS (ES+) 334.1551; C20H20O2N3 requires 334.1550, [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.

A common heterocyclic compound, 402-61-9, name is 5-Methyl-1H-pyrazole-3-carboxylic acid, molecular formula is C5H6N2O2, 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. 402-61-9.

General procedure: To a solution of 5-methyl-1H-pyrazole-3-carboxylic acid (19; 1.1-3.3 equiv) in DMF (5 mL) were added EDCI¡¤HCl (1.1-3.3 equiv), HOBt¡¤H2O (1.1-3.3 equiv) and DIPEA (1.1-3.3 equiv) at 0 C and the resulting mixture was stirred at this temperature for 30 min. The corresponding derivative bearing one to three amino groups (17, 25-28 or 36; 1 equiv), dissolved in DMF (1 mL), was added and the reaction mixture was stirred for 48 h at r.t. After this time, the reaction mixture was poured into ice-water (30 mL) and the formed precipitate was filtered off and washed thoroughly with small amounts of distilled H2O to free it from DMF. After drying in a dessicator, the desired products were obtained as white solids.

The synthetic route of 5-Methyl-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

35344-95-7, 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 35344-95-7 as follows.

1-(2-Hydroxyethyl)-1H-pyrazole-4-carbaldehyde In a 30-mL sealed tube, 1H-pyrazole-4-carbaldehyde (500 mg, 5.20 mmol, 1.00 equiv), potassium carbonate (1.08 mg, 7.80 mmol, 1.50 equiv) and 2-bromoethan-1-ol (775.3 mg, 6.20 mmol, 1.19 equiv) were mixed in CH3CN (10 mL) at room temperature. The reaction mixture was then irradiated with microwave for 40 min at 150¡ã C. After the reaction was done, the reaction mixture was cooled to room temperature, filtered through a celite pad and the filtrate was concentrated under reduced pressure. The residue was purified in a silica gel column eluting with dichloromethane/methanol (1percent to 5percent gradient) to afford 1-(2-hydroxyethyl)-1H-pyrazole-4-carbaldehyde (650 mg, 89percent) as yellow solid. MS: m/z=140.8 [M+H]+

According to the analysis of related databases, 1H-Pyrazole-4-carbaldehyde, the application of this compound in the production field has become more and more popular.

5334-43-0, Name is 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile, 5334-43-0, 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.

General procedure: To a stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

Statistics shows that 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 5334-43-0.