Tag: M.W:100-200

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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., 5334-40-7

Step 1: Into a 250 mL round bottom flask containing a suspension of 4-nitro-1H-pyrazole-3- carboxylic acid (20.0 g, 127 mmol) in methanol (100 mL) was added concentrated sulfuric acid (4 mL) dropwise over 5 min at 0 oC and the resulting slurry was refluxed at 80 oC for 16 h. The solvent was removed under reduced pressure and the residual mass was dissolved in ethyl acetate (300 mL) and washed with saturated aqueous sodium bicarbonate solution (2 x 100 mL) and brine (100 mL) and dried over anhydrous sodium sulfate. The solution was filtered and concentrated under reduced pressure to give methyl 4-nitro-1H-pyrazole-3-carboxylate as a solid. The crude product was taken to the next step without further purification. MS calc?d [M- H]+ 170.0, found 170.0.

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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. 1134-50-5 name is 1-Phenyl-1H-pyrazole-4-carboxylic acid, 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. 1134-50-5

[00240j To a solution of 1-phenyl-1H-pyrazole-4-carboxylic acid (590 mg, 3.1 mmol) in THF (6.9 mL) at rt was added borane-THF complex (6.2 mL, 6.2 mmol, 1 M in THF), and the reaction mixture was stirred over night. The mixture was quenched by the slowaddition of 1M NaOH and pouring into water. The mixture was extracted with ether (2x). The combined organics were washed with water and brine, dried over Na2SO4, andconcentrated to give Example 22A a white solid. MS (ESI) m/z 175.1 (M+H). The crude product was used in the next synthetic step without further purification.

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

25016-11-9, 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. 25016-11-9 name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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 intermediate 10b (200 mg), 1-methyl-i H-pyrazole-4-carboxaldehyde (183 mg; 1.66 mmol) and AcOH (32 jiL; 0.555 mmol) in DCE (6 mL) was stirred at 50Cfor 2 hours. The reaction mixture was cooled to room temperature and NaBH(OAc)3 (353 mg; 1.665 mmol) was added. The reaction mixture was stirred at room temperature overnight, poured onto a 10% aqueous solution of K2C03 and extracted with DCM. The organic layer was decanted, dried over MgSO4, filtered and evaporated to dryness. The residue was purifed by chromatography over silica gel (irregular SiOH,24g; mobile phase: gradient from 0% NH4OH, 0% MeOH, 100% DCM to 1% NH4OH,10% MeOH, 90% DCM). The pure fractions were collected and evaporated to dryness yielding 165 mg of compound 28 as an oil (73%). Compound 28 was dissolved in ACN and HC1 (4N in dioxane) (277 jiL; 1.11 mmol) was added. The HC1 salt was filtered but revealed to be too hydroscopic. The residue was then dissolved inDCM/MeOH and the organic layer was washed with a 10% aqueous solution of K2C03, dried over MgSO4, filtered and evaporated to dryness. The resulting residue was dissolved in ACN and fumaric acid (47 mg; 0.404 mmol; 1 eq) was added and the solution was allowed to stand until crystallization (overnight). The precipitate was filtered, washed with ACN then Et20 and dried yielding 188 mg of compound 28 as thefumarate salt (1 equivalent based on 1H NMR).

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

A common compound: 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, belongs to pyrazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 139756-02-8

Synthesis of BJ Step 7. 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (1 eq) and 4-methoxy-3-nitrobenzaldehyde (1.1 eq) were suspended in ethanol 5 ml and the mixture heated at 75 C for 2 hours after conformation of forming of imine by TLC. Added CuC12 (3 eq) and the reaction mixture heated at 75 C under 02 for 2 hours. Aftercompletion of the reaction, the ethanol was removed under vacuum. Then workup with ethyl acetate and water. Separate the organic layer and Water layer re-extracted with 2×25 ml ethyl acetate. The combined organic layers are washed with brine solution, concentrated under vacuum. The residue was purified by column chromatography on silica the desired product Bf as a brown solid; yield 88%. ?H NMR (400 MHz, DMSO)6: 12.54 (s 1H) 8.61 (s, 1H), 8.37 (d J=8.8 Hz 1H), 7.39 (d, J8.8 Hz 1H), 4.13 (s, 3H),3.84 (s, 3H), 2.78(t J=7.4Hz 2H), 1.76(m 2H), 0.95(tJ= 7.4Hz 3H). MASS: ESI [M +H] . 344.13; Elemental anal. calcd. for C16H17N504 C, 55.97; H, 4.99; N, 20.40; 0,18.64; found C, 55.87; H, 5.03; N, 20.43; 0, 18.67.

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, 139756-02-8, other downstream synthetic routes, hurry up and to see.

The chemical industry reduces the impact on the environment during synthesis 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, I believe this compound will play a more active role in future production and life. 139756-02-8

General procedure: A mixture of 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide 1a (1.0 mmol), Ketones 2(1.0 mmol) and InCl3 (10 mol%,) in acetonitrile (6 mL) was stirred at room temperature for the time indicated in Table 3. After completion of the reaction (indicated by TLC) the reaction mixture was filtered and wash with acetonitrile (2 X 5 mL) to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid isolated was triturated with MTBE (10 mL), filtered and dried to give the desired product.

The chemical industry reduces the impact on the environment during synthesis 139756-02-8. I believe this compound will play a more active role in future production and life.

10010-93-2, 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. 10010-93-2 name is 3-Methyl-5-(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.

a) A mixture of potassium carbonate (924 mg, 6.69 mmol), 2-methyl-5-(trifluoromethyl)-1H-pyrazole (501 mg, 3.34 mmol) and methyl 2-bromobutyrate (0.42 mL, 3.7 mmol) in dimethylformamide:tetrahydrofuran (3 mL:6 mL) was heated at 60 C. for 5 h with stirring. After cooling to room temperature, most of tetrahydrofuran was removed by gently blowing nitrogen over the reaction mixture. Ethyl acetate and water were added and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 12-17% ethyl acetate in hexanes) to afford the desired product (704 mg, 2.81 mmol, 84%).

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

82560-12-1, Name is 3-Amino-5-tert-butylpyrazole, 82560-12-1, 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.

3-(tert-butyl)-lH-pyrazole-5-amine (1.00 g, 7.18 mmol), 3-bromo-5- hydroxypyridine (1.14 g, 6.53 mmol), copper (I) iodide (62.0 mg, 0.33 mmol), K2CO3 (1.90 g, 13.7 mmol) and trans-N, N’-dimethylcyclohexane- l ,2-diamine (186 mg, 1.31 mmol), were weighed in a 20 mL microwave vial fitted with a stirrer bar and sealed with a crimped septum. The vial was then evacuated and purged with N2, and anhydrous toluene (10 mL) added. The resulting mixture vacuum degassed and purged with N2, and then heated at 100C for 24 h. The resulting dark suspension was diluted with EtOAc and filtered through Celite, washed with EtOAc and the filtrates concentrated in vacuo. The resulting residue was purified by FCC, eluting with 0-8% MeOH/DCM, to afford the title compound (1.15 g, 76%). LCMS (Method 3): t 2.31 min, m/z 233.2 [MH+]. NMR (300 MHz, CDC13): 1.32 (9H, s), 3.49 (1H, s), 5.55 (1H, s), 7.37 (1H, t, J = 2.3 Hz), 8.04 (1H, d, J = 2.5 Hz), 8.27 (1H, d, J = 2.1 Hz).

Statistics shows that 3-Amino-5-tert-butylpyrazole is playing an increasingly important role. we look forward to future research findings about 82560-12-1.

Adding some certain compound to certain chemical reactions, such as: 1125-29-7, name is 1,3,5-Trimethyl-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 1125-29-7. 1125-29-7

General procedure: To a solution of (S)-2,7-dimethyl-3-(3,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine (15 mg, 53.3 mumol) (Intermediate 40) in CH2Cl2 (0.48 mL) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (prepared according to methods described in Pat. Pub. No. WO2012145581, Oct. 26, 2012) (12.2 mg, 58.7 mumol), HATU (26.4 mg, 69.3 mumol), and N,N-diisopropylethylamine (27.6 muL, 0.16 mmol). After stirring at room temperature for 30 min, the mixture was concentrated in vacuo and purified by preparative HPLC (XBridge C18 column (5 mum, 100*4.6 mm), mobile phase of 5-95% ACN in 20 mM aqueous NH4OH) to afford the title compound as a white powder (21 mg, 84% yield). MS (ESI): mass calcd. for C23H18F4N6O, 470.1; m/z found, 471.2 [M+H]+. 1H NMR (600 MHz, DMSO-d6) delta 8.19-8.05 (m, 1.62H), 7.93-7.90 (m, 0.40H), 7.87-7.83 (m, 0.91H), 7.74-7.66 (m, 1H), 7.59-7.38 (m, 3H), 5.59-5.49 (m, 0.74H), 4.73-4.62 (m, 0.28H), 4.57-4.51 (m, 0.17H), 3.81 (s, 2.26H), 3.76 (s, 0.22H), 3.70 (s, 0.52H), 3.64-3.52 (m, 0.72H), 3.38-3.17 (m, 0.73H), 3.07-3.00 (m, 0.22H), 2.84-2.76 (m, 0.15H), 2.71-2.60 (m, 0.63H), 2.45-2.22 (m, 1.47H), 1.47 (d, J=6.7 Hz, 2.28H), 1.35 (d, J=6.8 Hz, 0.6H).

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 1,3,5-Trimethyl-1H-pyrazole-4-carboxylic acid.

A common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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. 4522-35-4.

l-(But-3-en-l-yl)-3-iodo-lH-pyrazole. To a solution of 5-iodo-lH-pyrazole (1.34 g, 6.91 mmol, 1 equiv) in DMF (23 mL) was added 60% NaH (0.33 g, 8.29 mmol, 1.2 equiv). After 10 min, 4-bromobut-l-ene (0.84 mL, 8.29 mmol, 1.2 equiv) was added. After stirring 3 d, the reaction was added to water and extracted with EtOAc (x3). The combined EtOAc extracts were dried (Na2S04) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-100%) EtOAc in hexane) to provide a 3: 1 mixture of product isomers (1.12 g, 65%>) as a colorless oil. Major isomer: 1H NMR (400 MHz, CDC13) delta 7.21 (d, J= 2.3 Hz, 1H), 6.39 (d, J= 2.3 Hz, 1H), 5.80 – 5.68 (m, 1H), 5.13 – 5.05 (m, 2H), 4.20 (t, J= 7.2 Hz, 2H), 2.61 (qt, J= 7.0, 1.3 Hz, 2H). Minor isomer: 1H NMR (400 MHz, CDC13) 7.53 (d, J= 1.8 Hz, 1H), 6.42 (d, J= 1.8 Hz, 1H), 5.81 (ddt, J= 17.1, 10.2, 6.9 Hz, 1H), 5.14 – 5.05 (m, 2H), 4.27 (t, J= 7.3 Hz, 2H), 2.65 – 2.58 (m, 2H).

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

5334-43-0, 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 5334-43-0 as follows.

EXAMPLE 3 1-Phenyl-4-cyano-5-(dicyclohexylaminosulfonylureido)pyrazole STR108 4.4 ml (50 mmol) of chlorosulfonyl isocyanate were added to a solution of 9.2 g (50 mmol) of 1-phenyl-4-cyano-5-aminopyrazole in 100 ml of methylene chloride. Stirring was carried out for 30 minutes at about 20 C., after which a solution of 7.5 ml (60 mmol) of triethylamine and 10 ml (50 mmol) of dicyclohexylamine in 50 ml of methylene chloride was slowly added dropwise. After the end of the addition, stirring was continued for a further hour and hydrolysis was then carried out with 200 ml of water. The organic phase was separated off and was worked up in a conventional manner to give the product. Yield: 87%.

According to the analysis of related databases, 5334-43-0, the application of this compound in the production field has become more and more popular.