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. 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 112758-40-4

To a solution of 3 -methyl- lH-pyrazole-4-carbaldehyde (1 g, 9.08 mmol) in acetonitrile (10 mL) is added potassium carbonate (1.76 g, 12.71 mmol) and 2,3- difluornitrobenzene (1.73 g, 10.90 mmol) and the mixture is stirred at room temperature overnight. Water is added and the organic phase is extracted with ethyl acetate. Organic layer is dried over sodium sulfate and the solvent evaporated under reduced pressure. The residue is purified by normal phase Isco chromatography using as eluent ethyl acetate/hexane (20-80%) to give a 62% yield of a mixture of regioisomers containing the title compound as major product that is used with no further purification. NMR is consistent with desired structure, although mixture of regiosomers is detected: NMR (MeOD): 9.98 (s, 1H), 8.65 (d, 1H, J= 1.6 Hz), 7.99-7.26 (m, 3H), 2.49 (s, 3H). A mixture of l-(2-fluoro-6-nitro-phenyl)-3 -methyl- lH-pyrazole-4-carbaldehyde (620 mg; 2.49 mmol) (as major compound in a mixture of regioisomers in the pyrazole) and Iron (1.40 g) in ethanol (5.1 mL) and water (5.1 mL) with few drops of acetic acid is heated at 90C for 2h. After that time, it is filtered over celite, and eluted with more ethanol. Mixture is concentrated under vacuum, basified with sodium bicarbonate (saturated aqueous solution) and extracted with dichloromethane. Organic layer is decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure to give 500 mg of the title compound, as major product in a mixture of regioisomers in the pyrazole, that is used without further purification. MS (m/z): 220 (M+l). To a solution of l-(2-amino-6-fluoro-phenyl)-3-methyl-lH-pyrazole-4- carbaldehyde (500 mg, 2.28 mmol) (as major compound in a mixture of regioisomers in the pyrazole) in dichloromethane (15.21 mL), pyridine (553.31 muKappa) is added. Then, methyl chloroformate (194.17 mu) is added dropwise at 0C and the mixture is stirred at room temperature for 30 min. Water is added and the mixture is extracted with dichloromethane. Organic layer is decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure. The residue is purified by normal phase Isco chromatography using as eluent ethyl acetate and hexane to give 418 mg of the title compound. MS (m/z): 278 (M+l). To a solution of methyl N-[3-fluoro-2-(4-formyl-3-methyl-pyrazol-l- yl)phenyl]carbamate (335 mg, 1.2 mmol) (as major compound in a mixture of regioisomers in the pyrazole) in tetrahydrofuran (6 mL) under nitrogen atmosphere and cooled to 0C, sodium hydride (60% in mineral oil) (58.3 mg) is added. Then, methyl iodide (0.4 mL) is added and the reaction mixture is stirred at 0C for 1 hour. After that time, water is added and the mixture is extracted with ethyl acetate. Organic layer is decanted, dried over sodium sulfate and solvent evaporated. The residue is purified by normal phase Isco chromatography using as eluent ethyl acetate and hexane to give 287 mg of the title compound, as major product in a mixture of regioisomers in the pyrazole, that is used without further purification. MS (m/z): 292 (M+l). To a solution of 2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′- piperidine] (210 mg, 0.75 mmol) in dichloromethane (3.00 mL), methyl N-[3-fluoro-2-(4- formyl-3-methyl-pyrazol-l-yl)phenyl]-N-methyl-carbamate (284.27 mg) (as major compound in a mixture of regioisomers in the pyrazole) is added. The mixture is stirred 10 min at room temperature. Then, sodium triacetoxyborohydride (331.5 mg) is added, and the reaction is stirred at room temperature overnight. The mixture is diluted with dichloromethane and quenched slowly with sodium bicarbonate (saturated solution). The organic phase is then extracted with more dichloromethane, decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure. The residue is purified by normal phase Isco chromatography using as eluent dichloromethane and methanol to give 160 mg of methyl N-[2-[4-[(2-chloro-4,4-difluoro-spiro[5H-thieno[2, 3-c]pyran-7,4′- piperidine]- -yl)methyl]-3-methyl-pyrazol-l-yl]-3-fluoro-phenyl]-N-methyl-carbamate. MS (m/z): 555 (M+l).The tartrate salt is essentially prepared as described in Example 1. MS (m z): 555 (M+l).

The synthetic route of 112758-40-4 has been constantly updated, and we look forward to future research findings.

Application of 162758-35-2, 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. 162758-35-2 name is 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-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.

To a suspension of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (3.82 g, 10 mmol) in toluene (75 ml) was added thionyl chloride (3.64 ml, 50 mmol) and the mixture was refluxed for 3 hours and then cooled to the room temperature. The solvent was evaporated off under the reduced pressure. The residue was redissolved in toluene (30 ml) and the solvent was evaporated off again (procedure repeated twice) to yield the carboxyl chloride (3.94 g, 98% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Some common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-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. category: pyrazoles-derivatives

Dissolve [2-(3′-chloro-2,3,5,6-tetrahydro-[l,2′]bipyrazinyl-4-yl)-ethyl]-methyl- amine hydrochloride salt (1.0 g, 2.57 mmol) in dichloromethane (20 ml) and cool in an ice-bath. Add triethylamine (1.79 ml, 12.87 mmol) and then 1 -methyl pyrazole-4- sulfonyl chloride (465 mg, 2.57 mmol). Remove the ice-bath and allow to warm to ambient temperature and allow to stir for 20 hr. Wash the combined organic layers with aqueous sodium bicarbonate, brine and water. Dry over sodium sulfate and concentrate. Purify by chromatography, eluting with 1:2 hexanes: acetone to afford the title compound (1.1 g, 97 % yield) as a white foam. MS ES: m/z = 400 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288148-34-5, its application will become more common.

Some common heterocyclic compound, 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, molecular formula is C6H7ClN2O, 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: 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde

General procedure: All reactions were carried out in vials under nitrogen atmosphere. Step 1: A solution of compound 8 (100 mumol, 1.0 equiv) and compound 9 (150 mumol, 1.5 equiv) in DMF (0.1 M) was treated with K2CO3 (300 mumol, 3.0 equiv) and stirred at 110 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 10. The crude aldehyde 10 (100 mumol, 1.0 equiv) was dissolved in acetone:water (2:1, 0.1 M) and treated with KMnO4 (600 mumol, 6 equiv) and stirred at 30 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 11. The crude acid 11 (100 mumol, 1.0 equiv) was treated with HATU (120 mumol, 1.20 equiv) followed by the crude amine (100 mumol, 1.0 equiv) and NEt3 (300 mumol, 3.0 equiv). The reaction was stirred at 30 C for 16 h (LCMS check). The reactions were concentrated and purified directly by reversed phase preparative HPLC using a C18 column and eluting with acetonitrile-water (0.225% formic acid or pH = 10 NH4OH) gradient. All compounds were deemed greater than 95% purity by LCMS and HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27006-76-4, its application will become more common.

Some common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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. Application In Synthesis of 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4149-06-8, its application will become more common.

Synthetic Route 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.

4-Bromopyrazole (1. 0g, 6. [8MMOL)] and triethylamine (0. [90MOL,] 6. [5MMOL)] were stirred under nitrogen in DMF at [0C.] Trityl chloride (1.81g, 6. [5MMOL)] was added, and the mixture was stirred for two days at room temperature. The mixture was then diluted with chloroform (10 [ML),] and washed with water. The organic portion was dried over sodium sulphate and solvent evaporated in vacuo to give the crude product. The resulting solid was washed with di-isopropyl ether to give the title compound (1.55g) LCMS RT 4.09min, [CPh3] + 243

Statistics shows that 4-Bromo-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 2075-45-8.

Electric Literature of 741717-63-5, A common heterocyclic compound, 741717-63-5, name is Ethyl 1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, molecular formula is C13H11F3N2O2, 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.

A mixture of ethyl l-phenyl-3- (trifluoromethyl) -IH- pyrazole-4-carboxylate (6.60 g, 23.2 mmol) and ethylenediamine (50 ml, 23.2 mmol) was heated at reflux for 3 hours. The mixture was concentrated under reduced pressure to a residue. To the residue was added toluene (50 mL) that was concentrate off, twice. The crude solid was dried under high vacuum overnight to give N- (2-aminoethyl) -l-phenyl-3-(trifluoromethyl) -lH-pyrazole-4-carboxamide (6.9 g, 99% yield) as a light tan solid. The desired product may also be isolated as the hydrochloride salt by dissolving in minimal DCM and adding IN HCl in Et2theta (3-5 molar equivalents) dropwise, filtering the solid and washing with Et2theta. 1H NMR (Free base analog) (DMSO-d6) delta 1.83 (br, 2H), 2.68 (t, J = 6.3 Hz, 2H), 3.21-3.26 (m, 2H), 7.47 (t, J = 7.4 Hz, IH), 7.60 (t, J = 8.0 Hzr 2H), 7.84 (d, J = 7.8 Hz, 2H), 8.29-8.30 (m, IH), 9.11 (s, IH); m/z (APCI pos) 299 (60%) (M+H) .

The synthetic route of 741717-63-5 has been constantly updated, and we look forward to future research findings.

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. 852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Computed Properties of C6H9ClN2

To a mixture of methyl ( 6-hydroxy-4-methyl-l- benzothiophen-3-yl) acetate (150 mg) and DMF (2 mL) were added 5- (chloromethyl) -1, 3-dimethyl-lH-pyrazole (101 mg) and K2C03 (175 mg). at room temperature. The mixture was stirred at room temperature for 3 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgS04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) . The product was crystallized from Et20-hexane to give the title compound (155 mg) . 1H NMR (300 MHz, CDC13) delta 2.26 (3H, s), 2.64 (3H, s) , 3.70-3.75 (3H, m) , 3.84 (3H, s) , 4.01 (2H, s) , 5.01 (2H, s), 6.10 (1H, s) , 6.76-6.81 (1H, m) , 7.10 (1H, s) , 7.23 (1H, d, J = 2.3 Hz).

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.

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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Iodo-1-methyl-1H-pyrazole

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

According to the analysis of related databases, 39806-90-1, the application of this compound in the production field has become more and more popular.

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 20055-01-0 as follows. COA of Formula: C4H10N4O4S

To a solution of (2S)-2- [ (BENZYLOXYCARBONYL) AMINO]-6- [ (TERT- butoxycarbonyl) amino] hexanoic acid (19.02 g) and triethylamine (5.56 g) in tetrahydrofuran (200 ml) was added methyl chloroformate (4.21 ml), followed by stirring under ice-cooling for 30 minutes. To the reaction mixture was added a solution of 1-METHYL-LH- pyrazole-4,5-diamine sulfate (15.75 g) and triethylamine (15.2 g) in water (50 ml) at the same temperature. The mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added chloroform (300 ml), and the layers were separated. The organic layer was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of 1- benzyl 5-tert-butyl (lS)- {l- [ (5-amino-l-methyl-lH- pyrazol-4-yl) CARBAMOYL] PENTAMETHYLENE} biscarbamate as an oil. The crude product was used directly in the next step without further purification. To a solution of the crude product of 1-benzyl 5- tert-butyl (LS)-{1-[(5-AMINO-1-METHYL-LH-PYRAZOL-4- yl) CARBAMOYL] PENTAMETHYLENE} BISCARBAMATE IN. methanol (350 ml) was treated with 10% palladium on carbon (2.0 g) under a hydrogen atmosphere at room temperature for 6 days. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate and dried in vacuo to give tert-butyl (5S)-5-amino-6- [ (5-amino-l-methyl-lH-pyrazol-4- yl) amino] -6-oxohexylcarbamate (12.1 g) as a solid. H-NMR (DMSO-D6) 6 1. 24-1. 40 (4H, m), 1. 36 (9H, s), 1. 70- 1.77 (2H, m), 2.88-2. 91 (2H, m), 3.51 (3H, s), 3.80-3. 82 (1H, m), 5.15 (2H, s), 6.77 (1H, br), 7.27 (1H, s), 10.05 (1H, br)

According to the analysis of related databases, 20055-01-0, the application of this compound in the production field has become more and more popular.