Category: pyrazoles-derivatives

Application of 6314-23-4,Some common heterocyclic compound, 6314-23-4, name is 2-(1-Pyrazolyl)ethanol, molecular formula is C5H8N2O, 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.

General procedure: 30 g (0.2 mol) of phosphorus oxychloride was added to a mixture of 11.2 g of (0.1 mol) of 2-(1H-pyrazol-1-yl)ethanol I and 95.0 g (0.6 mol) of DMF upon stirring at 90C (maintaining the temperature below 120C). The reaction mixture was stirred during 1 hour at 100C, cooled, and neutralized with aqueous Na2CO3. The reaction product was extracted with chloroform and dried over magnesium sulfate. After removing the solvent, the residue was distilled in vacuum. Yield 9.7 g (75%), bp 47-48C (1 mmHg), nD20 1.5020, d420 1.1190 g/mL. IR spectrum, nu, cm-1: 1520 (ring). 1HNMR data coincided with that in [6].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1-Pyrazolyl)ethanol, its application will become more common.

Related Products of 473528-88-0, 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. 473528-88-0, name is 4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-bromo-l-methyl-lH-pyrazole-5-carbaldehyde (2.50 g, 13.2 mmol), bis- (pinacolato)diboron (5.04 g, 19.8 mmol), KOAc (3.89 g, 39.7 mmol) and PdCl2(dppf) (0.484 g, 0.661 mmol) in 1 ,4-dioxane (50 mL) was degassed and then heated at 80 C under N2 for 18 h, then was cooled to RT. The reaction mixture was diluted with EtOAc, then was filtered and concentrated in vacuo. The residue was chromatographed (80 g Si02; continuous gradient from 0% to 50% EtOAc in hexane over 20 min) to give the title compound (3.0 g, 12.7 mmol, 96 % yield) as a white solid. NMR (400 MHz, CDCls) d 10.27 (s, 1H), 7.78 (s, 1H), 4.19 (s, 3H), 1.34 (s, 12H); nB NMR (128 MHz, CDC13) d 29.2 (br s, IB).

The synthetic route of 4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde has been constantly updated, and we look forward to future research findings.

Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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: C14H19N3

To a solution of 3-tert-butyl-l-p-tolyl-lH-pyrazol-5-amine (102.9 g, 448.9 mmol) in EtOAc (1 L) at 10.9 0C was added a NaOH solution (2.5 M5 269 mL), and the biphasic reaction mixture warmed to 15.9 and then stabilized. Phenyl chloroformate (98.4 g, 156.5 mmol) was added in one portion and the temperature rose to 25.5 and then stabilized. The ice bath was removed and the reaction was monitored by HPLC. After 1 hour an additional 25 mL of 2.5 M NaOH was added. The reaction mixture was stirred overnight, and then diluted with EtOAc (200 mL). The organic layer was washed with brine (1 L)5 dried over Na2SO4 (200 g) and concentrated to about 400 to 500 mL of EtOAc. The concentrated solution was warmed to 60 0C. After the solids had dissolved, heptane (2 L) was slowly added, during which solids formed. After stirring for 30 minutes the solid was collected via filtration and the cake was washed with 400-500 mL of heptane. The cake was dried in a vacuum oven at ambient temperature to yield 156.9 g (95.0%) of the title compound. 1H NMR (400 MHz3 CDCl3) delta 7.39 – 7.31 (m, 6H), 7.26-7.225 (m, 2H), 7.13 (br s, 2H)5 6.96 (br s. IH), 6.47 (br s, IH), 2.42 (s, 3H), 1.34 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 285984-25-0, its application will become more common.

Related Products of 16617-46-2,Some common heterocyclic compound, 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, molecular formula is C4H4N4, 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 30; (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-l-yl)pyrazolori,5-alpyrimidine-3-carboxamide; Step A: Preparation of 5-hydroxypyrazolo[l,5-alpyrimidine-3-carbonitrile.; To a mixture of 5-amino-lH-pyrazole-4-carbonitrile (2.70 g, 25.0 mmol) and CS2CO3 (16.3 g, 50.0 mmol) in dry DMF (70 mL) was added ethyl 3-ethoxyacrylate (5.41 g, 37.5 mmol) and the mixture was heated at 100 0C for 4 hours. The mixture was cooled to ambient temperature and the resultant slurry was poured into deionized H2O (150 mL). The resulting aqueous solution was cooled on an ice bath and concentrated HCl was added slowly with mixing to pH = 3.5. The resulting precipitate was collected, washed with H2O followed by Et2O. The solid was dried in vacuum to afford the product as a light beige powder (3.87 g, 97percent). MS (apci) m/z = 159.0 (M-I).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-1H-pyrazole-4-carbonitrile, its application will become more common.

Application of 930-36-9, These common heterocyclic compound, 930-36-9, name is 1-Methylpyrazole, 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 1. Synthesis of 2-methyl-2H-pyrazole-3-carbaldehyde In a dry 50 ml Vial is placed a solution of 1.642 g (20 mmol) N-Methylpyrazole in 30 ml dry THF. The mixture is cooled to -20 C and while stirring 8 ml (20 mmol, 2.5M in hexane) n-BuLi-solution is slowly added. The reaction mixture is stirred for 2.5 h at -20 C. With vigorous stirring 4.7 ml (4.39g, 60 mmol) dry DMF is slowly added at -20 C and the mixture kept at this temperature for 1 h. The reaction mixture is then poured into 100 ml of a 1 M acetic acid / sodium acetate buffer (pH: 4.5), 50 ml MTBE is added and the organic layer is separated, washed with 50 ml sat. Na2CO3-solution to remove excess acetic acid (extraction with ethyl acetate leads to DMF in the final product). The organic layer is separated, dried with MgSO4 and the solvent is removed by om a rotary evaporator. The crude product is purified by vacuum distillation (bp: 67 C, 21 mbar). 3 preparations which were distilled together yielded 5.969g (54 mmol, 90%) of the title compound. 1H-NMR (300 MHz, CDCl3): 4.18 (s, 3H, CH3-N), 6.91 (d, 1H, 3J=2.0 Hz, CH=C-N), 7.53 (d, 1H, 3J=2.0 Hz, CH=N), 9.87 (s, 1H, CH=O) ppm. 13C-NMR (100 MHz, CDCl3): 39.31 (CH3-N), 114.78 (CH=C-N), 138.54 (CH=N), 138.98 (CH=C-N), 179.83 (CH=O) ppm.

Statistics shows that 1-Methylpyrazole is playing an increasingly important role. we look forward to future research findings about 930-36-9.

Related Products of 92933-47-6, A common heterocyclic compound, 92933-47-6, name is 5-Isopropyl-1H-pyrazole-3-carboxylic acid, molecular formula is C7H10N2O2, 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.

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%). 1H NMR (300 MHz, DMSO-d6) ppm 13.00 (s, 1H), 11.93 (s, 1H), 7.98 (d, J = 7.40 Hz, 2H), 7.67 (t, J = 7.15 Hz, 1H), 7.59 (t, J = 7.47 Hz, 2H), 6.40 (s, 1H), 5.18 (br. s., 0.9H), 4.75 (br. s., 1.1H), 4.20 (br. s., 1.2H), 3.93 (br. s., 0.8H), 2,91-3.10 (m, 1H), 2.78 (br. s., 2H), 1.25 (d, J = 5.7 Hz, 6H). 13C NMR (101 MHz, DMSO-d6) ppm 166.7, 164.5, 146.7, 147.0, 139.5, 139.2, 133.3, 132.7, 131.0, 128.8, 125.9, 114.3, 104.1, 95.6, 44.0, 41.5, 25.6, 25.4 22.7. LC/MS (ESI+, MeCN/H2O): m/z: calcd for C22H21N5O2S: 419.14 [M+H]+; found: 420.1.

The synthetic route of 92933-47-6 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, 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 127107-23-7, Application In Synthesis of 1-Methyl-1H-pyrazol-4-amine hydrochloride

Synthesis of Compound 1-8. Into a 25-mL round-bottom flask, was placed 8.5 (50 mg, 0.15 mmol, 1.00 equiv), l-methyl-lH-pyrazol-4-amine hydrochloride (30 mg, 0.22 mmol, 1.50 equiv), K3P04 (99 mg, 0.45 mmol, 3.00 equiv), Xphos-Pd (13 mg, 0.10 equiv) in tert-butanol (5 mL). The resulting solution was stirred for 4 h at 80 C. The resulting mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with dichloromethane/methanol (20: 1). This resulted in 34 mg (58%) of 1-8 as a yellow solid. LC-MS (ESI, m/z): 398 (M+H+); MR (300 MHz, CD3OD) delta 8.62 (s, 1H), 7.94 (s, 1H), 7.86 (s, 1H), 7.65 (s, 1H), 4.24 (m, 1H), 3.98 (m, 4H), 3.89 (s, 3H), 3.42 (s, 4H), 2.34 (m, 4H), 1.53-1.76 (m, 4H).

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Related Products of 118430-74-3, 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. 118430-74-3, name is 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 168 Synthesis of N-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-8-methoxy-5H-pyrido[4,3-b]indol-1-amine (Cpd. No. 255) In a round bottom flask, 4-(1-chloro-8-methoxy-5H-pyrido[4,3-b]indol-7-yl)-3,5-dimethylisoxazole (10 mg, 0.03 mmol), 3-cyclopropyl-1-methyl-1H-pyrazol-5-amine (9.06 mg, 0.06 mmol) and sodium tert-butoxide (11.5 mg, 0.12 mmol) were dissolved in dry toluene (10 mL). A solution of Pd2(dba)3 (10.8 mg, 0.012 mmol) and Dave Phos (9.4 mg, 0.024 mmol) in dry toluene (5 mL) was heated to reflux for 5 mins in a two-neck container before it was transferred into the round bottom flask by needle syringe. The resulting mixture was vacuumed and protected with nitrogen balloon, and heated to reflux overnight. As the reaction reach completion, the system were acidified with trifluoroacetic acid and concentrated in vacuum. The residue were dissolved in MeOH/H2O (3:1) system, filtered and purified by prep-HPLC. The product was lyophilized to give the title compound as a color-less powder (2.4 mg, yield 18.7%). 1HNMR (300 MHz, MeOD-d4) delta 8.01 (s, 1H), 7.80 (d, 1H, J=7.2 Hz), 7.56 (s, 1H), 7.37 (d, 1H, J=7.2 Hz), 6.24 (s, 1H), 3.98 (s, 3H), 3.80 (s, 3H), 2.36 (s, 3H), 2.19 (s, 3H), 2.00 (m, 1H), 1.00 (m, 2H), 0.81 (m, 2H). ESIMS m/z [M+H]+ calcd.=429.49. found=430.17.

The synthetic route of 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine 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. 632365-54-9, name is Methyl 5-amino-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 5-amino-1H-pyrazole-3-carboxylate

[00126] delta-Amino-S-pyrazolcarboxylic acid methyl ester (16.91 g, 119.8 mmol) is dissolved in ethanol (2.4 L) and hydrochloric acid (37%, 12.5 ml_, 150 mmol) is added. Then, a solution of 2-bromo-malonaldehyde (18.9 g, 125.2 mmol) in ethanol (1.4 L) and is quickly added in a dropwise manner at RT. After 30 min, a precipitation is observed; after 6 hours the precipitate is filtered and washed with 50 mL ethanol and thereafter with 50 mL diethyl ether to give 4.19 g of 6-bromo-pyrazolo[1 ,5a]pyrimidine-2-carboxylic acid methyl ester. After evaporation of the filtrate and crystallisation, an additional 1.43 g of product is obtained. Totally 5.62 g (18.3 %).

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.

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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O

To a solution of l,3-dimethyl-li/-pyrazole-4-carbaldehyde (1.00 g, 8.06 mmol) in nitromethane (35 mL) was added ammonium acetate (0.155 g, 2.01 mmol). The reaction mixture was heated at reflux overnight. Excess nitromethane was removed under reduced pressure. The residue was purified by automated flash silica column chromatography (40 g column) eluting with a gradient of 20-50% EtOAc in heptanes. The fractions were evaporated to give the title compound as a yellow solid (1.31 g, 97%). ESI-MS [M+H]+ calc?d for C7H9N3O2, 168.08; found, 168.2.

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.