Category: pyrazoles-derivatives

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

General procedure: To a mixture of carboxylic acid (1 mmol), EDC¡¤HCl (1.2 mmol) and HOBt (1.2 mmol) in dry dichloromethane (10 mL) was added a mixture of amine (1 mmol) and triethyl amine (1.5 mmol) in dichloromethane (5 mL) at 0 C. The mixture was stirred at room temperature till the completion of reaction (judged by TLC). The reaction mixture was diluted with additional DCM (20 mL). The organic layer was washed with water, brine and dried (Na2SO4). Concentration and purification over silica gel (100-200 mesh) afforded the desired compound.

Statistics shows that 162758-35-2 is playing an increasingly important role. we look forward to future research findings about 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid.

Adding some certain compound to certain chemical reactions, such as: 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic 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 3112-31-0. 3112-31-0

A procedure identical with that of 1 was followed for the preparation of 4, except that CuSO4¡¤5H2O was replaced by Cu(NO3)2¡¤3H2O (0.121g, 0.5mmol), purple microcrystals were obtained (yield: 74percent, based on Cu(NO3)2¡¤3H2O). Elem. Anal. Calcd for C15H16CuDy2N6O18: C 18.51, H 1.68, N 8.73. Found: C 18.62, H 1.71, N 8.64. IR (KBr pellet cm?1): 3420(s), 1630(s), 1592(s), 1509(m), 1392(m), 1326(s), 1271(m), 1062(w), 1015(w), 853(w), 782(w).

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 1H-Pyrazole-3,5-dicarboxylic acid.

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. 139756-02-8, name is 4-Amino-1-methyl-3-N-propyl-1H-pyrazole-5-carboxamide, This compound has unique chemical properties. The synthetic route is as follows., 139756-02-8

General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2mol%), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2¡Á5mL) and acetone (2¡Á5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

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1192-21-8, A common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, molecular formula is C4H7N3, 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.

Heat a solution of 2,4-dichloropyridine (15.3 g, 103 mmol), L-methyi5 aTninopyrazole (ii g, 113 mmoi), cesium carbonate (6 g, 10 nimol) and tris(dibenzyiideneacetone)dipaiiadium(0) (4.7 g, 5 mmoi) in 1 ,4dioxane (750 niL) in asealed vessel at 75 ¡ãC overnight. Cool the reaction to room temperature and dilute with water (1.5 L). Extract the mixture with three portions DCM, Filter the aqueous layer to remove solids and extract the filtrate with two portions EtOAc. Combine all organic extracts, dry over magnesium sulfate, filter and concentrate the filtrate. Purify the residue by silica gel column chromatography by loading the product onto a 260 g pre-coiumn andeluting the pre-colunin onto a 750 g column with a gradient from 1-5percent MeOH in DCM to give the title compound 16.8 g (78percent). MS (m/z): 209 (M+i),

The synthetic route of 1-Methyl-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below.

Step B: 1-({2-tert-Butyl-1-[(trans-4-fluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)-1H-pyrazole-4-carbaldehyde2-tert-Butyl-1-[(4-fluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (400 mg, 1.03 mmol), pyrazole-4-carboxaldehyde (300 mg, 3.09 mmol) (see Example 126, step H for preparation) and DMAP (catalytic) were stirred in 10 mL of DCM containing DIPEA (0.90 mL, 5.15 mmol) at rt for 3 h. The solution was washed with saturated aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography on silica gel using hexanes/EtOAc (1:1) as eluent. Yield: 131 mg (28percent). 1H NMR (400 MHz, CHLOROFORM-D) delta 1.16-1.26 (m, 2H), 1.35-1.48 (m, 2H), 1.54-1.56 (m, 9H), 1.72 (dd, J=8.69, 3.03 Hz, 2H), 1.95-2.04 (m, 1H), 2.11-2.19 (m, 2H), 4.17-4.21 (m, 2H), 4.37-4.46 (m, 1H), 4.50-4.59 (m, 1H), 7.44 (d, J=8.59 Hz, 1H), 7.96 (dd, J=8.69, 1.86 Hz, 1H), 8.08 (s, 1H), 8.44 (d, J=1.37 Hz, 1H), 8.64 (s, 1H), 9.91 (s, 1H).

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4522-35-4, Adding a certain compound to certain chemical reactions, such as: 4522-35-4, name is 3-Iodo-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 4522-35-4.

INTERMEDIATE 61 4-(3-Iodo-lH-pyrazol-l-yl)-N,N-dimethylpyrimidin-2-amine NaH (119 mg, 60% in oil, 2.97 mmol) was added to a solution of 3-iodo-lH-pyrazole (480 mg, 2.48 mmol) in anhydrous DMF (10 mL) at 25 C under N2. The mixture was stirred for 10 min and 4-bromo-N,N-dimethylpyrimidin-2-amine (500 mg, 2.48 mmol) was added. The resulting mixture was stirred for another 2 h at 25 C under N2. The reaction mixture was then quenched with saturated aq. NH4C1 solution and extracted with with EtOAc. The organic layer was washed with brine, dried (Na2S04) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Isco Combiflash Rf, RediSep Silica 40 g, 30% EtOAc in hexanes, then 30-100% EtOAc in hexanes) to afford 4-(3-iodo-lH-pyrazol-l-yl)-N,N- dimethylpyrimidin-2-amine. LCMS calc. = 314.99; found = 315.99 (M+H)+.

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

Some common heterocyclic compound, 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, molecular formula is C11H5Cl2F3N4, 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. 120068-79-3

Example 1; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with triethylamine hydrochloride, sodium trifluoromethylsulfinate and thionylchloride, in 6.5 molar equivalents of tolueneWithin a 3-neck, 50 ml. round bottom flask equipped with a magnetic stirrer bar and a thermometer were placed vacuum dried sodium trifluoromethylsulfinate (4.29 g, 27.5 mmol), vacuum dried triethylamine hydrochloride (5.16 g, 37.5 mmol), and 13 ml. an- hydrous toluene (6.5 molar equivalents relative to 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H-pyrazole-3-carbonitrile) under an argon atmosphere. After cooling to 00C to 5 0C with an ice bath, thionylchloride (3.57 g, 30 mmol) was added slowly while keeping the reaction temperature below 5 0C. After stirring for another 30 min, vacuum dried 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-1 H-pyrazole-3- carbonitrile (8.03 g, 25 mmol, 99 % purity) was added at 5 0C, and the reaction mixture was heated to 50 0C within 5 min by a preheated water bath. The temperature of 50 0C was kept for another 6 hours before quenching the reaction with 50 ml. of saturated NaHCO3 solution. The resulting suspension was diluted with 30 ml. of ethylacetate. After phase separa- tion the organic layer was washed once with saturated NaHCtheta3 solution and concentrated under reduced pressure until dryness. The crude product was crystallized from refluxing toluene (100 g) affording the title compound as a white crystalline powder (8.06 g, 70 % yield, 94 % purity by quantitative HPLC). 1H-NMR (Bruker DRX-500, d6- DMSO): delta [ppm]: 8.33 (s), 7.57 (s).; Example 12; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H-pyrazole-3- carbonitrile with trimethylamine tosylate, sodium trifluoromethylsulfinate and thionyl- chloride, in 6.5 molar equivalents of tolueneThe preparation procedure was conducted as described above for example 1. The crude product was crystallized from refluxing toluene (100 g) affording the title compound as a white crystalline powder (76 % yield, 96 % purity by quantitative HPLC).; Example 14; Sulfinylation of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1 H- pyrazole-3-carbonitrile with trimethylamine tosylate, sodium trifluoromethylsulfinate and thionylchloride, in 6.5 molar equivalents of tolueneThe preparation procedure was conducted as described above for example 11. The crude product was crystallized from refluxing toluene (100 g) affording the title com- pound as a white crystalline powder (73 % yield, 98 % purity by quantitative HPLC).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 120068-79-3, its application will become more common.

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. 5334-40-7 name is 4-Nitro-1H-pyrazole-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. 5334-40-7

Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and EPO dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (1H NMR (400 MHz, DMSOd6) delta 14.4 (s, IH), 9.0 (S5 IH)3 4.4 (q, 2H), 1.3 (t, 3H)).

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

These common heterocyclic compound, 402-61-9, name is 5-Methyl-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. 402-61-9

General procedures for Example 168-185; To a solution of 168a (13 mg, 0.02 mmol) in DMA in a 4 ml vial was added the acid monomer (0.025 mmol) dissolved in DMA followed by a solution of HATU (0.025 mmol) in DMA and then triethylamine (0. 4 mmol) neat. The vial was capped and microwaved at 150 C for 30 minutes. The reaction was checked by LC/MS and concentrated to dryness. The residue was dissolved in MeOH:DMSO (1:1 v:v, 1.5 ml) and purified by reverse phase HPLC.HPLC condition: Samples were purified by preparative HPLC on a Phenomenex Luna C8(2) 5 um 100A AXIA column (30mm x 75mm). A gradient of methanol (A) and 0.1%trifluoroacetic acid in water (B) was used, at a flow rate of 50mL/min (0-0.5 min 20% A, 0.5- 6.0 min linear gradient 20-100% A, 6.0-7.0 min 100% A, 7.0-8.0 min linear gradient 100- 10% A).; Example 168; (2R,6S,13aS,14aR,16aS,Z)-2-(3-ethyl-8-fluoroquinoxalin-2-yloxy)-6-(5-methyl-lH- pyrazole-3-carboxamido)-N-(l-methylcyclopropylsulfonyl)-5,16-dioxo- 1, 2,3,5, 6,7, 8,9, 10,11, 13a,14,14a,15, 16, 16a-hexadecahydrocyclopropa[e]pyrrolo[l, 2- a] [ 1 ,4] diazacyclopentadecine- 14a-carboxamide; The title compound 168 was prepared according to the general procedure used for Example 168-185 using 5-methyl-lH-pyrazole-3-carboxylic acid as the acid monomer. MS (ESI): m/z = 765.3 [M+H].

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 402-61-9.

35344-95-7,Some common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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.

To the stirred solution of cyclopentyl methanesulfonate 6-3 (380 mg, 2.31 mmol) in DMF (2 mL) was added lH-pyrazole- 4-carbaldehyde 6-4 (266.81 mg, 2.78 mmol) and cesium carbonate (1.51 g, 4.63 mmol) at 0C. The reaction was heated at 80C for 16 hours and then diluted with ice cold water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude material was purified by flash chromatography using Q%~3()% ethyl acetate/hexane to afford -cyciopentylpyrazole-4-carbaldehyde 5 (280 mg, 1.71 mmol, 73.69% yield) as a brown liquid. H I NMR (400 MHz, DMSO-d6) 6 9.77 (s, 1 1 1), 8.50 (s, 1 1 1 ), 7.98 (s, lH), 4 80-4 73 (m, 1H), 2.13-2.05 (m, 2H), 1 98-1.87 (m, 2H), 1.83-1.77 (m, 21 1), 1.69-1.67 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Pyrazole-4-carbaldehyde, its application will become more common.