Category: pyrazoles-derivatives

Electric Literature of 1018446-95-1, 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. 1018446-95-1 name is tert-Butyl 4-amino-1H-pyrazole-1-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 microwave tube was added 4-bromo-2-(2, 6-dichlorophenyl)-lH-imidazo-[4,5- c]-pyridine (0.050 g, 0.15 mmol), tert-butyl-4-amino-lH-pyrazole-l-carboxylate (0.032 g, 0.17 mmol), Pd2(dba)3 (0.013 g, 0.015 mmol), XantPhos (0.017 g, 0.03 mmol), Cs2C03 (0.098 g, 0.03 mmol) and dioxane (1.2 niL). The mixture was degassed with N2 for 1 min. The resulting mixture was irradiated in a microwave reactor at 160 C for 2 housr and then cooled to room temperature. The mixture was filtered with Celite and the filtrate was concentrated by vacuum. The residue was purified by prep-HPLC (Gilson GX 281 , Shim- pack PRC-ODS 250 mm x 20 mm x 2, gradient: CH3CN / 10 mm/L NH4HC03, 17 min) to give the desired product (15 mg, 15% yield). ? NMR(MeOD- 4, 500 MHz): delta 8.09 (s, 1H), 7.90 (d, J = 5.5 Hz, 1H), 7.76 (s, 1H), 7.59 (m, 3H), 6.97 (d, J = 5.5 Hz, 1H). LCMS(ESI) m/z: 345.2 [M+H+].

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

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. 49633-25-2, name is 3-Isopropylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 49633-25-2

To a solution of 2,4-dichloro-7-methoxyisoquinolin (0.54 g, 2.36 mmol) in DMF (5 ml) was added Cs2CO3 (1.54 g, 4.74 mmol) followed by 3-isopropyl-1H-pyrazole (0.78 g, 7.10 mmol). The reaction mixture was heated to 80 C. for 18 h. The reaction mass was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and then concentrated under reduced pressure to get crude compound. The crude compound was silica gel chromatography to get desired compound (0.1 g, 14%) as white solid. 1H NMR (400 MHz, CDCl3): delta ppm 8.60 (d, J=2.51 Hz, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 8.07 (d, J=9.04 Hz, 1H) 8.15 (s, 1H) 7.26 (s, 2H) 7.16-7.22 (m, 1H) 6.35 (d, J=2.51 Hz, 1H) 3.97-3.99 (m, 4H) 3.10 (quin, J=7.03 Hz, 1H) 1.36 (s, 4H) 1.34 (s, 3H). MS: MS m/z 302.1 (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 49633-25-2.

Electric Literature of 1029413-53-3,Some common heterocyclic compound, 1029413-53-3, name is tert-Butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate, molecular formula is C12H20N4O2, 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.

Step 3: Preparation of 1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine A reaction flask containing a suspension of LAH (499 mg, 13.2 mmol) in THF (22 mL) was evacuated and back-filled with nitrogen three times. A solution of tert-butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate (830 mg, 3.3 mmol) in THF (11 mL) was added dropwise, via an addition funnel and the reaction mixture was stirred at rt under nitrogen overnight. The reaction was quenched sequentially with water (1 mL), 1N NaOH (1 mL), and water (3 mL) to afford a suspension. The precipitate was filtered off and washed with ethyl acetate. The combined filtrates were diluted with a small amount of water and transferred to a separatory funnel. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The organics were combined and concentrated to give crude material (137 mg). To recover product in the aqueous layer, the aqueous extraces were lyophilized to give a solid residue. This was suspended in EtOAc and filtered. The filtrate was evaporated to give additional crude material (287 mg). The combined crude was purified via Biotage flash chromatography (25S column, eluting with 7 N NH3/MeOH in DCM (1%-4%)) to give the title compound (279 mg, 51% yield). m/z (APCI+) for C8H14N4 167.2 (M+H)+. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.89-2.00 (m, 1H) 2.20-2.31 (m, 1H) 2.26 (s, 3H) 2.42 (td, J=8.40, 6.19 Hz, 1H) 2.60 (dd, J=9.60, 4.80 Hz, 1H) 2.64-2.77 (m, 2H) 3.79 (br. s., 2H) 4.67 (m, J=9.44, 7.23, 4.67, 4.67 Hz, 1H) 6.87 (s, 1H) 7.07 (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 tert-Butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate, its application will become more common.

These common heterocyclic compound, 23170-45-8, name is Methyl 3-methyl-1H-pyrazole-4-carboxylate, 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. HPLC of Formula: C6H8N2O2

General procedure: Compound (11a-g or 12f-g) (1.2 mmol), CuI (19.1 mg, 0.1 mmol), trans-N,N’-dimethyl-1,2-cyclohexane-diamine (29 mg, 0.2 mmol), K2CO3 (0.29 g, 2.1 mmol) and DMF (3 mL) were added to a tube filled with argon. The mixture was stirred at 110 C for 24 h. The reaction was diluted with H2O (20 mL) and extracted with EtOAc (15 mL x 2). The combined organic phases were washed with H2O (20 mL x 2) and brine (30 mL), dried over MgSO4 and concentratedin a vacuum. The residue was purified by flash column chromatography (12-25% EtOAc in petroleum ether).

The synthetic route of Methyl 3-methyl-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

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 18213-75-7 as follows. Computed Properties of C5H8N4O

Example 1.2.: 1-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (3) 7 g (50 mmol) of 5-amino-1-methyl-1H-pyrazole-4-carboxamide (2) is mixed with an excess of urea (50 g) and the mixture is heated at 200C for 3 h. The reaction cake is cooled to RT and the residue is dissolved in 500 mL of chloroform. The organic phase is washed with 5% aqueous acetic acid. The organic phase is separated and the solvent is evaporated. The title compound is purified by crystallization from water.

According to the analysis of related databases, 18213-75-7, the application of this compound in the production field has become more and more popular.

27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, 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. Safety of 1-Methyl-1H-pyrazole-5-carbaldehyde

General procedure: A mixture of the corresponding secondary phosphinechalcogenide1 (1.00 mmol) and carbaldehyde2 or 4 (1.05 mmol) in toluene(2 ml) was stirred at 23-50 C for 6 to 94 h in argon atmosphere (seeOnline Supplementary Materials for details). Toluene was removed undervacuum, and the residue was washed with Et2O (1 ml), dissolved in CHCl3and re-preciptatedwith n-hexane. The resulting solid was collected, driedunder vacuum to afford alcohols 3 or 5.

The synthetic route of 27258-33-9 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. 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Safety of 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid

11) 3-(tert-butyl)-N-(3-chloro-4-methylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of the Acid (257 mg, 1.41 mmol, 1.1 eq) in DMF (10 mL) was added an amine (200 mg, 1.29 mmol, 1.0 eq), DIEA (830 mg, 6.43 mmol, 5 eq) and HBTU (584 mg, 1.54 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (30 mL) and washed with 10% aqHCl (1*25 mL), sat NaHCO3 (1*25 mL) and water (4*25 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (10% to 50% EtOAc in Hexane) to give the amide as a colorless solid in 66% (165 mg, >95% purity). Mass Spectrum (LCMS, ESI Pos.) Calcd. For C17H23ClN3O: 320.0 (M+H), Found 320.0.

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. 92933-47-6, name is 5-Isopropyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Isopropyl-1H-pyrazole-3-carboxylic acid

General procedure: To a solution of HATU (174.17 mg, 0.459 mmol) and 3-isopropylpyrazole-5-carboxylic acid (59.85 mg, 0.388 mmol) in DMF (2 mL) was then added diisopropylethylamine (92 muL, 0.529 mmol). The reaction solution was stirred at room temperature for 2 h. The N-(3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)benzamide (100 mg, 0.353 mmol) was added in one portion. The solution was then stirred at room temperature overnight. The reaction was diluted with methylene chloride and washed. The aqueous layer was extracted with methylene chloride twice, the combined organic phases were dried over anhydrous MgSO4. After evaporation of the solvent and recrystallization from ethyl acetate, filtered and dried to give desired compound (50 mg, 34%).

According to the analysis of related databases, 92933-47-6, the application of this compound in the production field has become more and more popular.

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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine

N- (5-TERT-BUTVL-2-P-TOLVL-2H-PVRAZOL-3-VL)-2-F 4-F2-MORPHOLIN-4-VL-ETHOXV- naphthalen-1-yl]-2-oxo-acetamide, (13); Compound 12 (0. 224 g, 0. 653 mmol) was dissolved in THF (20 mL). To this solution was added 1 N LIOH (3 eq, 1. 96 mmol). The solution was allowed to stir for 2 hours then neutralized with 4 N HCl in dioxane and the solvent was evaporated providing a white solid. The residue was dried under high vacuum at 80C for 30 minutes and then suspended in CH2C12 (50 mL). To the suspension was added oxalyl chloride (0. 56 mL, 6. 53 mmol) and few drops of DMF. The suspension was stirred at room temperature for 2 hrs then the solvent evaporated. The resulting solid was suspended in ethyl acetate (20 mL) and added to 5-AMINO-3-T-BUTYL-L- (4-METHYLPHENYL) pyrazole (1) (0. 159 g, 0. 663 mmol) dissolved in ethyl acetate (20 mL) and a 50% NAHC03 solution (10 mL) and stirred overnight at 60C. The mixture was diluted with ethyl acetate and extracted with NaHCO3. The combined organic layers were washed with brine, dried over MGS04, filtered and the solvent removed leaving a brown oil. The material was purified by column chromatography (50-100% EtOAc/Hexanes) or (0-5% methanol/DCM) providing 0. 346 g (98%) of the desired compound as a yellow solid. LC-MS : Calculated mass= 540. Observed mass= 541.

According to the analysis of related databases, 285984-25-0, the application of this compound in the production field has become more and more popular.

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. 400877-57-8, name is Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

To a mixture of methyl -1-methyl-4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 19 (0.95 g, 5.1 mmol) and THF (25 mL)-methanol (5 mL), 1N aqueous sodium hydroxide solution (8.0 mL) was added, and the mixture was stirred at room temperature for 2 hr. The mixture was acidified with hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.69 g, yield 79%). 1H-NMR (CDCl3) :delta 4.08(3H, s), 8.28 (1H, s).

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 400877-57-8.