Day: June 22, 2021

These common heterocyclic compound, 51985-95-6, name is Methyl 5-hydroxy-1-methyl-1H-pyrazole-3-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. Product Details of 51985-95-6

Methyl 5 -hydroxy- i-methyl- 1H-pyrazole-3 -carboxylate (I Med. Chem., 54:8174 (2011)) (0.35 g, 2.24 mmol), K2C03 (0.62 g, 4.48 mmol), and sodium chlorodifluoroacetate (0.684 g, 4.48 mmol) were dissolved in DMF (10 mL) and water (1 mL). The reaction was heated to 130 °C for 20 mm. The reaction was diluted with water (100 mL) and EtOAc (200 mL). The organic phase was separated, washed with water(5x) and brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (0-80percent EtOAc/Hex gradient) to give Intermediate 14A (0.3 73 g, 81percent yield) as a colorless syrup. MS(ESI) m/z: 207.0 (M+H) ?H NMR: (400 MHz, CDC13) oe ppm 6.44 (t, J=i.0 Hz, 1H), 6.46 (t, J=72.2 Hz, 1H), 3.92 (s, 3H), 3.82 (s, 3H); ?9F-NMR:(376 MHz, CDC13) oe ppm -84.02 (s, 2F).

The synthetic route of Methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 92-43-3, name is 1-Phenyl-3-pyrazolidinone, 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 92-43-3, Computed Properties of C9H10N2O

1-Phenylpyrrolidin-3-one (82.99mmoM.0eq)Dissolved with 5% aqueous sodium hydroxide solution,Add ferric chloride hexahydrate (16.60 mmol, 0.2 eq), and pass the system to oxygen and keep the temperature at 80 C. After the reaction is completed, add water to the reaction solution to quench the reaction, and adjust RhoEta=1~2 with hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.Concentrated under reduced pressure, and the residue was purified by column chromatography (eluent: PE: EpsilonAlpha = 2:1)The pale yellow solid product 1-phenyl-1H-pyrazol-3-ol (1.46 g, yield 11%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Phenyl-3-pyrazolidinone, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Taihe International Trade Co., Ltd.; Du Yonglei; Lv Liang; Li Hongwei; Liu Shiqin; Liu Jiyong; Hou Shuang; Ma Wen; (36 pag.)CN108503587; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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.

General procedure: The aqueous solution of Eu(NO3)3.6H2O (1mmol) was treated with threefold excess of ethanolic solution of HIPA (3mmol) and the resulting mixture was thoroughly mixed on magnetic stirrer. The aqueous solution of NaOH was added drop wise to adjust the pH of mixture by 6-7. After constant stirring of 3 hr, off white precipitates of C1 binary complex were appeared which were isolated by vacuum filtration, washed with ethanol and water respectively, and then dried in desiccators.[19] Similarly, ternary complexes C2-C5 were synthesized by adding ethanolic solution of dmbipy, dipy, dmph and phen (1mmol) respectively, to the reaction mixture of europium(III) nitrate (1mmol) and ligand HIPA (3mmol) prior to adjustment of pH of the solution. Binary complex of gadolinium ion with ligand HIPA [Gd(IPA)3.2H2O] is synthesized by similar method as of C1 to calculate the triplet state of ligand. The synthetic routes of ligand HIPA and europium (III) complexes C1-C5 are shown in Fig. 1

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

Reference:
Article; Dhankhar, Priyanka; Bedi, Manisha; Khanagwal, Jyoti; Taxak, Vinod B.; Khatkar, Satyender P.; Doon, Priti Boora; Spectroscopy Letters; vol. 53; 4; (2020); p. 256 – 269;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1227611-94-0, name is 4-(4-Iodo-1H-pyrazol-1-yl)cyclohexanone, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11IN2O

Intermediate 21 and 22: cis and trans-4-(4-Iodo-pyrazol-1-yI)-cyclohexanol Sodium borohydride (86 mg; 2.27 mmol; 0.5 eq.) was added portionwise to a suspension of 4-(4-lodo-pyrazol-1-yl)-cyclohexanone (1.33 g; 4.55 mmol; 1.0 eq.) in EtOH (10 mL).The reaction mixture was stirred at RT for 30 mm and concentrated under vacuum. The residue was taken up with EtOAc (50 mL) and washed with NH4CI aq sat (50 mL). The aqueous phase was back-extracted with EtOAc (twice). Combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give 1.42 g of an oil. Purification by flash chromatography on silica (heptane/EtOAc, gradient from 80:20 to 40:60) afforded the title compounds.1st eluting compound: colorless glue (234 mg, 18%). Cis-4-(4-Iodo-pyrazol-1-yl)-cyclohexanol. HPLC (Condition A): Rt 2.69 mm (purity 99.7 %). MS (ESI+): 293.1.2nd eluting compound: white powder (730 mg, 55%). Trans-4-(4-lodo-pyrazol-1-yl)-cyclohexanol. HPLC (Condition A): Rt2.65 mm (purity 100 %). MS (ESI+): 293.1.

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 1227611-94-0.

Reference:
Patent; ARES TRADING S.A.; CROSIGNANI, Stefano; JORAND-LEBRUN, Catherine; GERBER, Patrick; MUZERELLE, Mathilde; WO2014/8992; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 34334-96-8, 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 34334-96-8 as follows.

Add acetonitrile (45 mL) to a mixture of 5-rnethyi-3-nitro-IH-pyrazoie (1.2 g, 9.0 rnmoi). potassium carbonate (2.5 g, 2.0 eq). and (S)-1-chloro-2-propanol (().98 g, 1.2 eq). Stir at 85 C for four days. Cool to a Filter to collect the solid and rinse the solid with EtOAc, then discard the solid. Collect and concentrate the filtrate n vacuo to provide aresidue. Subject the residue to normal phase chromatography, eluting with 50% EtOAc in hexanes. to give the title compound as a white solid (1.1 g, 67%). MS (ES) m/z 186 (4+H)

According to the analysis of related databases, 34334-96-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie Anne; CLAYTON, Joshua Ryan; COATES, David Andrew; SALL, Daniel Jon; WOODS, Timothy Andrew; (58 pag.)WO2018/13486; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 89088-55-1, 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 89088-55-1 as follows.

The solution of 4-(( 1 -methylpiperidin-4-yl)oxy)-3 -(trifluoromethyl)aniline (77 mg, 437.5 umol) and DIEA (106 mg, 820.3 umol, 143.2 uL) in DCM (3.0 mL) was cooled to – 30C for 0.5 h. Then triphosgene (53 mg, 180.4 umol) was added. The mixture was stirred at -30C for 1 h. Then a solution of 5-bromo-1-methyl-1H-pyrazol-3-amine (150 mg, 546.8 umol) in DCM (1.0 mL) was added. The resulting mixture was stirred at 25C for 1 h. MeOH (2 drop) was added and concentrated to get crude residue. The residue was purified by prep-TLC (Si02, Dichloromethane / Methanol = 10/1) to afford 1-(5-bromo-1-methyl-1H-pyrazol-3-yl)-3-(4-((1- methylpiperidin-4-yl)oxy)-3 -(trifluoromethyl)phenyl)urea (150 mg, crude).

According to the analysis of related databases, 89088-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (143 pag.)WO2018/222917; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1124-16-9, name is 5-Amino-1-isopropyl-3-methylpyrazole, 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 1124-16-9, Recommanded Product: 5-Amino-1-isopropyl-3-methylpyrazole

Example 41a 2-[(5-Chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide A microwave tube was charged with 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide (70 mg, 0.224 mmol), {3-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine (70 mg, 0.503 mmol) and cesium carbonate (230 mg, 0.706 mmol). The reaction mixture was degassed with nitrogen for 10 min. At same time, BINAP (50 mg, 0.080 mmol) and palladium(II) acetate (10 mg, 0.045 mmol) were added. The reaction mixture was heated in a microwave at 160 C. for 40 min. The crude material was purified on reverse-phase HPLC (Gilson) eluding with CH3CN/H2O with 0.1% formic acid which gave a title compound (15 mg, 15%); MS: M (C20H23ClN6O2)=414.89, (M+H)+=415, 416; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 9.42 (br. s., 1H) 8.71 (br. s., 1H) 8.02 (s, 1H) 7.54 (br. s., 1H) 7.06 (t, J=7.5 Hz, 1H) 6.48 (s, 1H) 6.32 (br. s., 1H) 5.86 (s, 1H) 4.47 (dt, J=13.4, 6.7 Hz, 1H) 3.92 (s, 3H) 2.26 (s, 3H) 1.41-1.43 (d, J=6.6 Hz, 2H).

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, 5-Amino-1-isopropyl-3-methylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ADAMS, Jerry Leroy; Faitg, Thomas H.; Johnson, Neil W.; Lin, Hong; US2010/113475; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 158001-28-6, 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 158001-28-6 as follows.

In a 100mL round-bottomed flask, add 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile (5g, 30.47mmol), 80mL formamide solution, and heat the mixture in an oil bath to 180 C. After about 5 h, the reaction was monitored by TLC (developer: PE / EtOAc = 1: 1). After the reaction solution was cooled, 50 mL of water and CH 2 Cl 2 (200 mL × 3) were added for extraction. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (eluent: PE / EtOAc = 4/1). -1/1) gave the product 1-tert-butyl-4-amino-1H-pyrazolo [3,4-d] pyrimidine as a white solid, 5.82 g, yield: 91%.

According to the analysis of related databases, 158001-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan University Huaxi Hospital; Chengdu Huaxi Jingzhun Medical Industrial Technology Institute Co., Ltd.; He Yang; Li Weimin; Shen Zhen; Chen Hai; Huang Ridong; Luo Yujiao; Zhou Xinglong; Chai Yingying; (26 pag.)CN110526921; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1572-10-7, name is 3-Amino-5-phenylpyrazole, A new synthetic method of this compound is introduced below., Formula: C9H9N3

General procedure: A mixture of appropriate aniline, p-toluidine, p-anisidine, 3-amino-5-phenylpyrazole or 3-aminol,2,4-triazole (5 mmol) and azido compound 20 (1.78 g, 5 mmol) in dry dioxane (20 mL) was refluxed for 4 h. The resulting solid, so formed, was collected and recrystallized gave 21a-d, respectively.

The synthetic route of 1572-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abdelriheem, Nadia Abdelhamed; Ahmad, Sayed Abdel-Kader; Abdelhamid, Abdou Osman; Molecules; vol. 20; 1; (2015); p. 822 – 838;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 27258-33-9,Some common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, molecular formula is C5H6N2O, 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 stirred solution of 2-Methyl- 2H-pyrazole-3-carbaldehyde (1.00 g, 0.0099 mol) in toluene (30 mL) was added Wittig salt (3.37 g, 0.0099 mol) at room temperature. To this resulted suspension was added DBU (1.52 mL, 0.0099 mole) drop wise and heated to reflux for 3 h. After completion of reaction toluene was distilled off completely under vacuum. Resulted crude oily mass was purified on combi flash. Pure Evaporation of solvent afforded compound 2 (0.450 g, 41.32% yield) as White Solid.Analytical data IH NMR (400 MHz, CDC13) delta: 3.93 (s, 3H), 5.75, 5.79 (s, s, IH total), 6.56- 6.57 (d, IH), 7.26, 7.30 (s, s, IH total), 7.46-7.47 (d, IH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-pyrazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; TAIT, Bradley; CULLEN, Matthew; WO2014/210159; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics