Category: pyrazoles-derivatives

Some common heterocyclic compound, 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C10H7ClN4, 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. Formula: C10H7ClN4

Example 9: Synthesis of 4-imino-l-phenyl-5-(2,3,6-trifluorophenyl)-4,5-dihydro-lH- pyrazolor3,4-dlpyrimidine-6(7H)-thione (A575 (33)):Synthesis of 4-imino-l-phenyl-5-(2,3,6-trifluorophenyl)-4,5-dihydro-lH-pyrazolor3,4- dlpyrimidine-6(7H)-thione (A575 (33)). A mixture of 5-amino-l -phenyl- lH-pyrazole-4 carbonitrile (218 mg, 1 mmol) and l,3,4-trifluoro-2-isothiocyanatobenzene (189 mg, 1 mmol) was refluxed for 2h,and then cooled. Intermediate was precipitated spontaneously and were collected as pure products (M+l)+ = 408 (325 mg, white solid, 80%). Then using the same procedure as that of A348 (13) to synthesis compound (A575 (33)) (M+l)+ = 498.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51516-67-7, its application will become more common.

Electric Literature of 930-36-9, 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 930-36-9 as follows.

The 6-[4-[4-[2-(l-methyl-lH-pyrazol-5-yl)ethoxy]phenyl]piperidin-l-yl]-3-(trifluoromethyl)[l,2,4]triazolo[4,3-b]pyridazine used as starting material was prepared as follows :-; Preparation of 2-(l-methyl-lH-pyrazol-5-yl)ethanol n-Butyl lithium (1.6M in hexanes) (1226 mL, 1961.78 mmol) was added dropwise to 1- methyl-lH-pyrazole (153.4 g, 1868.37 mmol) in THF (3000 mL) cooled to -78C over a period of 1 hour under nitrogen. The resulting solution was stirred at -600C for 30 minutes, then warmed to -100C and stirred for a further 40 minutes. A solution of oxirane (210 mL, 4203.82 mmol) in THF (600 mL) was added slowly at – 100C followed by further THF (1000 mL) and the resulting slurry was stirred at -100C for 30 minutes, then at 00C for 30 minutes. The mixture was then allowed to gradually warm to room temp under nitrogen and stirred for 16 hours. The reaction mixture was quenched with saturated NH4CI solution (2000 ml), the layers separated and the aqueous phase extracted with n-butanol (3 x 1000 ml). The combined organics were washed with saturated brine (1500 ml), dried over MgSOphi filtered and evaporated to give an oil, which was azeotroped with toluene(1000 ml) to leave an oil with some solid. The oil was dissolved in DCM and the insoluble solid was filtered off and washed with DCM. The filtrate was purified by chromatography using a silica Novasep prep HPLC column, eluting with a gradient of 5-10% methanol in DCM. Pure fractions were evaporated to dryness to afford 2-(l-methyl-lH-pyrazol-5- yl)ethanol (195 g, 83%) as an oil.IH NMR (400.1 MHz, DMSO-d6) delta 2.77 (2H, t), 3.63 (2H, m), 3.74 (3H, s), 4.74 (IH, t), 6.04 (IH, m), 7.26 (IH, d).

According to the analysis of related databases, 930-36-9, 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: 18952-87-9, name is 1-Isopropyl-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 18952-87-9, Formula: C6H10N2

2-Isopropyl-2H-pyrazole-3-boronic acid: n-BuLi (17.46 g, 110 ml, 273 mM, in hexanes) was slowly added over 30 minutes at -78C to a THF solution of 1-isopropyl-1H-pyrazole (25.0 g, 227 mmol). The reaction mixture was stirred at -78C for 2 hours. A solution of cooled triisopropoxy boronate (170.0 g, 909 mmol) was added slowly via canula over 45 minutes. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was adjusted to pH 6-7 with HCl (1M, 170 mL). The solvent was evaporated to dryness and the resulting residue was triturated with 1:1 ethylacetate:dichloromethane, the suspension filtered and the solvent was evaporated in vacuo to yield 2-isopropyl-2H-pyrazole-3-boronic acid as a colorless solid (20.0 g, 58%). LCMS m/z (%) = 154 M+H+, (100). 1H NMR (400 MHz, DMSO-d6) delta: 8.14 (s, 2H), 7.2 (s, 1H), 6.5 (s, 1H), 5.05 (m, 1H), 1.2 (d, J= 9.0 Hz, 6H).

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, 1-Isopropyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Electric Literature of 31108-57-3, The chemical industry reduces the impact on the environment during synthesis 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of IV-B8 (44 mg, 0.11 mmol) in acetone (2 mL) was added lH-pyrazole-4- carbonitrile (16 mg, 0.17 mmol) and K2C03 (48 mg, 0.34 mmol). After stirring at 25C for 12 h, the mixture was diluted with water (5 mL) and extracted with EtOAc (2 x 10 mL). The combined organic solution was washed with brine (5 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by flash column (0-43% of EtOAc in PE) to give IV-B9 (22 mg, 49%) as a solid. (3084) 1HNMR (400 MHz, CDCl3) dH 7.86 (s, 1H), 7.81 (s, 1H), 5.08-5.02 (m, 1H), 4.94-4.87 (m, 1H), 2.63 (t, j= 8.8 Hz, 1H), 2.26-2.16 (m, 1H), 2.06-1.99 (m, 1H), 1.82-1.70 (m, 6H), 1.46- 1.17 (m, 15H), 0.91-0.83 (m, 2H), 0.65 (s, 3H). LC-ELSD/MS purity 99%, MS ESI calcd. for C24H33N302 [M+H]+396.2, found 396.2

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, 1H-Pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 181585-93-3, 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. 181585-93-3 name is Methyl 5-nitro-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.

To a stirred solution of methyl 3-nitro-lH-pyrazole-5-carboxylate(A59, 25.0 g, 146.19 mmol) in methanol(500 mL) was added Pd/C(3.80 g, 36.54 mmol) under N2 atmosphere and the reaction mixture was stirred under H2 balloon pressure at room temperature for 4 h. After completion of reaction mixture filtered through celite bed and washed with EtOAc. The filtrate was concentrated to dryness. The residue was washed with n-pentane dried to get methyl 3-amino-lH-pyrazole-5-carboxylate A60 as a pale yellow solid. Yield: 18.0 g(87%) LC-MS(ES) m/z : 142.16[M+H]+.

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

Related Products of 4522-35-4,Some common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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.

INTERMEDIATE 20 4-(3-Iodo- lH-pyrazol-1 -yl)-2-(trifluoromethyl)pyridine To a solution of 3-iodopyrazole (0.70 g, 3.61 mmol), in DMSO (18.0 mL) was added sodium hydride (60% disp. in oil, 0.173 g, 4.33 mmol), and the resulting mixture was stirred for 0.5 h before adding 4-fluoro-2-trifluoromethyl pyridine (0.596 g, 3.61 mmol). The reaction mixture was stirred at 90 C for 3 h. The reaction was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO, 40 g, 0-50 % EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l-yl)-2-(trifluoromethyl)pyridine, as a white solid. LCMS calc. = 339.95; found = 339.93 (Mu+Eta)+. NMR (500 MHz, CDC13): delta 8.77 (d, J= 5.3 Hz, 1 H); 8.03 (d, J= 3.8 Hz, 1 H); 7.91 (d, J= 2.6 Hz, 1 H); 7.77 (d, J= 5.4 Hz, 1 H); 6.74 (d, J= 2.5 Hz, 1 H).

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

These common heterocyclic compound, 1621-91-6, name is 1H-Pyrazole-3-carboxylic acid, 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. Safety of 1H-Pyrazole-3-carboxylic acid

Example 10; Synthesis of (lR)-l-(l-naphthyI)-7V-({l-[4-(trifluoromethyl)phenyl]-lH-pyrazol-3- yl}methyl)ethanamineStep 1. A 500 mL round-bottomed flask was charged with l//-pyrazole-3-carboxylic acid 59 (5.0 g, 45 mmol), 100 mL of MeOH, and 10 drops of concentrated sulfuric acid. This mixture was heated to reflux and heating was continued for 12 h. After cooling to room temperature, the solvent was removed and the residue was dissolved in EtOAc and saturated aqueous NaHCO3. The layers were separated and the organic layer was dried and concentrated to give methyl lH-pyrazole-3-carboxylate 60.

The synthetic route of 1H-Pyrazole-3-carboxylic acid 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. 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 3112-31-0

(2R,3R)-3-Amino-4-(2-chloro-phenyl)-2-hydroxy-butyric acid ethyl ester (1.0 g, 3.9 mmol, 1.0 eq.), HATU (1.5 g, 3.9 mmol, 1.0 eq.), and 3,5-pyrazoledicarboxylic acid (0.6 g, 3.9 mmol, 1.0 eq.) were combined in DMF (5 mL) and stirred for 2 minutes. DIPEA (3.0 eq.) was added and the mixture was stirred for 1 hour then vacuumed to dryness. EtOAc (200 mL) was added and the mixture was washed with 1N HCl (100 mL), NaHCO3 (100 mL), and saturated aqueous NaCl (100 mL). The organic layer was retained and dried over anhydrous MgSO4 for 10 minutes prior to filtration and evacuation to dryness. The product was then treated with 1.25M HCl in EtOH (20 mL), heated to 100¡ã C. overnight, then vacuumed to dryness. The product was then purified by flash chromatography (0-75percent EtOAc/hexanes) to yield the title compound (1.1 g).

The synthetic route of 3112-31-0 has been constantly updated, and we look forward to future research findings.

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. 26621-44-3, name is 3-Nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Nitro-1H-pyrazole

K2003 (48.9 g, 353.8 mmol) is added to a solution of 3-nitro-1H-pyrazole (20.0 g,176.9 mmol) in THF (200 mL) followed by 2-bromo-ethanol (18.8 mL, 265.3 mmol) and the mixture is heated under reflux for 24 h. After cooling, the mixture is partitioned between water (200 mL) and EtOAc (200 mL). The phases are separated and the aqueous phase is extracted with EtOAc (2 x 200 mL). The combined organic phases aredried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified by trituration from Et20, the solid is collected by filtration and washed with Et20, DCM and Et20 again. The filtrate is concentrated in vacuo and is triturated from Et20. The solids are combined to give the title compound (18.1 g, 64 % yield) as an off-white solid.

According to the analysis of related databases, 26621-44-3, the application of this compound in the production field has become more and more popular.

Reference of 15754-60-6, 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 15754-60-6 as follows.

Intermediate 10: 4-Bromo-1-(1,1-dimethylethyl)-1H-pyrazole[0393]1-(1,1-dimethylethyl)-1H-pyrazole (6.1 g, 49.1 mmol) in dichloromethane (DCM) (200 ml) was added N-bromosuccinimde (8.74 g, 49.1 mmol). This was warmed to ambient temperature and stirred for 18 h. There was no starting material present and so the reaction mixture was quenched with aqueous sodium thiosulfate. The organics were washed with water (2¡Á500 ml) and passed through a hydrophobic frit. The filtrate was concentrated in vacuo to yield an orange-brown oil which turned purple on standing (7.402 g).[0395]LCMS (Method B): Rt=1.03 min, MH+=203, 205

According to the analysis of related databases, 15754-60-6, the application of this compound in the production field has become more and more popular.