Category: pyrazoles-derivatives

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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 39806-90-1

To a solution of 4-iodo-1-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles)and sodium carbonate (27.98 gm, 0.264 moles) wereadded. The reaction mixture was evacuated and backfihled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted withethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60-70C, cooled the mixture to 20-30C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30C. The solid product obtained was filtered, washedwith cold Dl water (100 ml) and dried at 40-50C to afford the product, I-Methyl-IHpyrazole-4-carbonitrile.Drywt : 17.94gmYield : 0.32 w/w (63%);

The synthetic route of 39806-90-1 has been constantly updated, and we look forward to future research findings.

20154-03-4, 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 20154-03-4 as follows.

Example 104: Preparation of (S)-3-methyl-2-(8-(3-(trifluoromethyl)-lH- pyrazol-l-yl)dibenzo[b,d]furan-3-sulfonamido)butanoic acidStep 1 : Preparation of (SWert-butyl 3-methyl-2-(8-(3-(trifluoromethvO-lH-pyrazol- l-yDdibenzo[b,d1furan-3-ylsulfonamido)butanoate[0234] (S)-Tert-butyl 2-(8-bromodibenzo[b,d]furan-3-sulfonamido)-3- methylbutanoate from (Example 103, Step 2, 485 mg, 1 mmol), 3- (trifluoromethyl)pyrazole (274 mg, 2 mmol), /roem’-N,N’-dimethyl-l,2- cyclohexanediamine (29 mg, 0.2 mmol), copper (I) iodide (CuI, 10 mg, 0.05 mmol), and K3PO4 (450 mg, 21 mmol) were mixed in 2 mL of toluene. The mixture was irradiated with microwave at 13O0C for 3 hours. The reaction mixture was purified by a preparative etaPLC to give 313 mg of (S)-/erf-butyl 3-methyl-2-(8-(3- (trifluoromethyl)-l/7-pyrazol-l-yl)dibenzo[b,d]furan-3-ylsulfonamido)butanoate as a white solid in 58percent yield.

According to the analysis of related databases, 3-(Trifluoromethyl)-1H-pyrazole, the application of this compound in the production field has become more and more popular.

113100-53-1, 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. 113100-53-1 name is 1-Methyl-3-(trifluoromethyl)-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.

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N’-[trans-4-(6-methoxy-3-methyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexanecarbonyl]-hydrazide Trans-N’-4-(6-Methoxy-3-methyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexanecarboxylic acid hydrazide (180 mg, 0.49 mmol), HATU (223 mg, 0.59 mmol), TEA (0.15 mL, 1.08 mmol) and 3-(trifluoromethyl)-1H-pyrazol-4-carboxylic acid (114 mg, 0.59 mmol) were dissolved in DMF (2 mL) and the mixture was left stirring overnight at r.t. The solvent was removed in vacuo and the crude was washed with MeOH to give the titled compound (75 mg, yield 33%). 1HNMR (DMSO) delta: 1.00-1.10 (2H, m), 1.27-1.37 (2H, m), 1.63-1.66 (2H, m), 1.73-1.76 (3H, m), 2.13-2.20 (1H, m), 3.27 (3H, s), 3.64 (2H, d, J=8.0 Hz), 3.74 (3H, s), 3.95 (3H, s), 6.62 (1H, dd, J=8.0 and 1.6 Hz), 6.85 (1H, d, J=1.6 Hz), 7.01 (1H, d, J=8.0 Hz) 8.32 (1H, s), 9.77 (1H, bs), 10.06 (1H, bs). C22H25F3N6O4 Mass (calculated) [508.50]. found [M+H+]=509, RT=1.17 (method f)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

Some common heterocyclic compound, 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, molecular formula is C12H12N2O3, 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. 83-10-3

To a suspension of 2-chloro-4-((7-methoxyquinolin-4-yl)oxy)aniline (190 mg, 0.63 mmol) and l,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-lH-pyrazole-4-carboxylic acid (161 mg, 0.69 mmol) in DCM (6 mL) was added EDCI (145 mg, 0.75 mmol) and HOAT (24mg, 0.17mmol). The reaction was heated to 46 C for 17 hours. Additional 1,5- dimethyl-3-oxo-2-phenyl-2,3-dihydro-lH-pyrazole-4-carboxylic acid (30 mg, 0.13 mmol) and EDCI (24 mg, 0.13 mmol) was added. The reaction was stirred further at 46 C for 5 hours, then cooled to rt, quenched with water (10 mL) and extracted with DCM (10 mL). The organic phase was washed with brine (20 mL x 3), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) = 60/1) to give the title compound as a light pink solid (150 mg, 46%). MS (ESI, pos. ion) m/z: 515.2 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-i): delta 2.72 (s, 3H), 3.35 (s, 3H), 3.94 (s, 3H), 5.76 (s, 1H), 6.56 (d, J = 5.2 Hz, 1H), 7.29 (m, 2H), 7.41 (d, J = 2.5 Hz, 1H), 7.46 (m, 2H), 7.54 (m, 2H), 7.60 (t, J = 7.5 Hz, 2H), 8.19 (d, J = 9.2 Hz, 1H), 8.63 (t, J = 7.0 Hz, 1H), 11.19 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 83-10-3, its application will become more common.

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. 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, A new synthetic method of this compound is introduced below., 120068-79-3

General procedure: A mixture of compound A (5 mmol) and corresponding benzaldehyde (5 mmol) in 10 mL ethanol was refluxed for 24 hours in a reaction flask wrapped up by silver paper. Upon the reactions completed (monitored by TLC), tawny solids were obtained through suction filtration. The precipitates were washed with ethanol (5 mLx3) and recrystallized from ethanol with 50-84% yields.

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.

16034-46-1, 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 16034-46-1 as follows.

To a solution of tert-butyl [2-(2,4-dichlorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (536 mg, 1.44 mmol) obtained in Example 155-D) in ethanol (0.9 mL) was added dropwise concentrated hydrochloric acid (3 mL) at 0C, and the mixture was stirred at room temperature for 15 min. The reaction mixture was cooled to 0C, neutralized with 8M aqueous sodium hydroxide solution (4.5 mL), adjusted to pH 10-11 with saturated aqueous sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in DMA (5 mL), and 1-methyl-1H-pyrazole-5-carboxylic acid (218 mg, 1.73 mmol) obtained in Example 1-A), HATU (658 mg, 1.73 mmol) and DIEA (0.126 mL, 0.72 mmol) were added at 0C. The reaction mixture was stirred at 60C for 3 hr, water was added, and the mixture was extracted twice with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (9:1-0:1)] and basic silica gel column chromatography [eluent: hexane-ethyl acetate (9:1-0:1)], and crystallized from ethyl acetate-hexane to give the title compound (314 mg) as yellow crystals (yield 57%). MS (ESI+): [M+H]+ 381. 1H NMR (300 MHz, CDCl3) delta 2.39 (3H, s), 4.20 (3H, s), 4.34 (2H, s), 6.67 (1H, d, J = 1.9 Hz), 7.15-7.36 (2H, m), 7.42 (1H, d, J = 2.3 Hz), 7.52 (1H, d, J = 1.9 Hz), 7.70 (1H brs).

According to the analysis of related databases, 1-Methyl-1H-pyrazole-5-carboxylic acid, the application of this compound in the production field has become more and more popular.

4522-35-4, Adding some certain compound to certain chemical reactions, such as: 4522-35-4, name is 3-Iodo-1H-pyrazole, 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 4522-35-4.

1-(chloromethyl)-4-methoxy-benzene (2.10 mL, 15.5 mmol) was added to a stirred mixture of 3-iodo-1H-pyrazole (2.01 g, 10.4 mmol) and Cs2CO3 (6.70 g, 20.6 mmol) in DMF (30.0 mL). The reaction mixture was stirred at 60 C for 2 hours and then, cooled to room temperature. Water (100mL) was added and aqueous was extracted with EtOAc (3 x 50 mL). Combined organic extracts were washed with aqueous saturated NH4Cl (25 mL) solution, brine (25 mL) and dried over MgSO4. The mixture was filtered and concentrated to afford 4.06 g of crude material. The residue was adsorbed on silica using DCM and purified by silica gel chromatography to afford 3-iodo-1-[(4- methoxyphenyl)methyl]pyrazole and 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole (3.18 g, 98%) as a white solid as a ca.5:1 mixture of regioisomers. Major Regioisomer: 1H NMR (400 MHz, CDCl3) 7.23 – 7.15 (m, 3H), 7.12 (d, J = 2.3 Hz, 1H), 6.92 – 6.85 (m, 2H), 6.40 (d, J = 2.3 Hz, 1H), 5.24 (s, 2H). : ESI-MS m/z calc.313.9916, found 314.98 (M+1)+; Retention time: 0.93 minutes Using Method J A mixture of tert-butyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (915 mg, 4.01 mmol), regioisomers mix of 5-iodo-1-[(4-methoxyphenyl)methyl]pyrazole/3- iodo-1-[(4-methoxyphenyl)methyl]pyrazole (1.51 g, 4.81 mmol), iodocopper (381.7 mg, 2.00 mmol), N,N’-dimethylethane-1,2-diamine (353.3 mg, 426.7 muL, 4.01 mmol) and K3PO4 (1.702 g, 8.02 mmol) in DMF (18.3 mL) was heated at 120 C for 3.5 hours. The reaction mixture was cooled to r.t. and filtered to remove the copper salts. The filtrate was diluted with water and aqueous was extracted twice with ethyl acetate. Organic extracts were washed with water, followed with brine, dried over Na2SO4, filtered and (0666) concentrated under reduced pressure. The recovered crude compound was purified by silica gel chromatography to give a mixture of the tert-butyl 4-[2-[(4- methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo-piperazine-1-carboxylate and the tert-butyl 4-[1-[(4-methoxyphenyl)methyl]pyrazol-3-yl]-2,2-dimethyl-3-oxo- piperazine-1-carboxylate (1.603 g, 96%). Major regioisomer: 1H NMR (400 MHz, DMSO-d6) 7.70 (d, J = 2.3 Hz, 1H), 7.22 – 7.11 (m, 2H), 6.91 – 6.81 (m, 2H), 6.61 (d, J = 2.3 Hz, 1H), 5.14 (s, 2H), 3.86 – 3.79 (m, 2H), 3.69 (s, 3H), 3.66 – 3.58 (m, 2H), 1.58 (s, 6H), 1.40 (s, 9H). ESI-MS m/z calc.414.2267, found 416.38 (M+1)+

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 4522-35-4.

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 20154-03-4 as follows. 20154-03-4

EXAMPLE 7 (5,11-Dihydro-pyrido[2,3-b][1,5]benzodiazepin-6-yl)-[2-trifluoromethyl-4-(3-trifluoromethyl-pyrazol-1-yl)-phenyl]-methanone Sodium hydride (60percent suspension in oil, 0.17 g, 4.25 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (10 mL). 3-trifluoromethyl pyrazole (0.34 g, 2.5 mmol) was added in one portion. After the gas evolution subsided stirring was continued at room temperature. The (5,11-dihydro-pyrido [2,3-b][1,5]benzodiazepin-6-yl)- (4-fluoro-2-trifluoromethyl-phenyl)methanone of Example 4, Step B (0.75 g, 1.94 mmol) was added in one portion and the mixture was placed in an oil bath (preheated at 130¡ã C.) overnight. After cooling, the mixture was partitioned between water and ethyl acetate. The organic extracts were dried over sodium sulfate, and evaporated to dryness in vacuo. The residue was crystallized from ethanol to yield the title compound (0.57 g, 57.3percent) as an off-white solid, m.p. 127-129¡ã C. NMR (DMSO-d6, 400 MHz): delta 4.19 and 5.46 (dd, 2H, CONCH2), 6.54 (m, 1H), 6.70 (m, 1H), 6.80 (m, 1H), 7.02 (m, 1H), 7.07 (m, 1H, pyrazole CH), 7.29 (m, 1H), 7.61 (m, 1H), 8.00 (m, 1H), 8.05-8.16 (m, 2H), 8.84 (m, 1H, pyrazole CH), 9.63 (s, 1H, NH) MS (EI, m/z): 503 [M]+ Anal. Calc’d for C24 H15 F6 N5 O: C 57.26, H 3.00, N 13.91. Found: C 57.07, H 2.97, N 13.58

According to the analysis of related databases, 20154-03-4, the application of this compound in the production field has become more and more popular.

2075-46-9, These common heterocyclic compound, 2075-46-9, name is 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.

Example 16 Preparation of 5-bromo-1H-pyrazol-4-amine, HBr A mixture of 4-nitro-1H-pyrazole (10 g, 88 mmol) and 5% palladium on Al2O3 (1 g) in a mixture of ethanol (150 mL) and 50% aqueous HBr (50 mL) was shaken in a Par apparatus under hydrogen (10 psi) for 36 h. The mixture was filtered and the catalyst washed with ethanol. The filtrate was concentrated in vacuo to give a white solid. This solid was suspended in 10 mL of ethanol. After swirling the flask for 5 min, ether was added to complete the crystallization. The solid was filtered, was washed with ether and dried under high vacuum to afford 5-bromo-1H-pyrazol-4-amine, HBr (18.1 g, 84% yield) as a white solid: mp 248 C. dec; 1H NMR (400 MHz, DMSO-d6) delta 11.47 (s, 1H), 10.00 (s, 1H), 7.79 (s, 1H).

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 2075-46-9.

5334-40-7, 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below.

Add 6.31 kg of raw material to a 100 L reactor, N,N-dimethylformamide (45 L), carbodiimide (6.59 kg), 1-hydroxybenzotriazole (4.65 kg), stirred for 0.5 h, The ice water bath was cooled to 0 to 10 C, and the starting material 1 (4.5 kg) was added in portions, and then the temperature was raised to 20-25 C, and the reaction was stirred for 16 hours. The reaction solution was added to 270 L of water, and a solid was precipitated, suction filtered, washed, and separated, and the organic phases were combined and dried

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.