Day: June 8, 2021

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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, A new synthetic method of this compound is introduced below., Formula: C5H9N3

Example 16; Synthesis of (S^-bis-trifluoromethyl-benzy^-t-Ccyclopentylmethyl-ethyl-amino)- ljS-dimethyl-lH-pyrazololS^-ZjJpyridine-S-ylmethyll-carbamic acid methyl ester; Step (i): Synthesis of N-(2,5-dimethyl-2H-pyrazol-3-yl)-acetamide; Pyridine (7,1 mL, 90 mmol) was added to a solution of 2,5-dimethyl-2H-pyrazol- 3-ylamine (10 g, 90 mmol) in acetic anhydride (46 mL) at 0 0C and the resulting mixture was stirred at room temperature for 30 min. The solvent was removed under vacuum to yield the title compound as a brownish liquid (13.7 g), yield: 100%. 1H NuMR (400 MHz, CDC13): delta 7.91 (bs, IH), 5.98 (s, IH), 3.67-3.56 (m, 3H), 2.19-2.11 (m, 6H). ES-MS m/z 154 (M++ 1, 100%).

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.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; BARUAH, Anima; DE, Dibyendu; KHANNA, Ish Kumar; PILLARISETTI, Sivaram; MAITRA, Santanu; ALEXANDER, Christopher, W.; SREENU, Jennepalli; DAGER, Indu; WO2006/73973; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 288-13-1, The chemical industry reduces the impact on the environment during synthesis 288-13-1, name is 1H-Pyrazole, I believe this compound will play a more active role in future production and life.

General procedure: At first [Cu(Im12)2]CuCl2 (0.5 mmol, 0.305 g) was added to a 25 mL round bottom flask containing water (4 mL), indole (0.117 g, 1 mmol) and iodobenzene (0.203 g, 1 mmol).K2CO3 (0.276 g, 2 mmol) and TBAB (0.322 g, 1 mmol) was added and the reaction stirred at 80 C for 12 h. The reaction progress was monitored by TLC(EtOAc/n-hexane; 1:3 v/v) and after completion, the organic phase was extracted from the ionic liquid with EtOAc (2 8 mL) and concentrated in vacuo. The promoter was used directly for the next run. The product was purified by silica gel column chromatography (EtOAc/n-hexane; 1:3 v/v). The isolated product was dried under vacuum overnight to give a yield of 92%. All products are known in the literature and were identified by comparison of their FT-IR, 1H, and 13C NMR spectra with the literature data.

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, 1H-Pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Heidarizadeh, Fariba; Majdi-Nasab, Afrooz; Tetrahedron Letters; vol. 56; 46; (2015); p. 6360 – 6363;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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 l,2,3,4-tetrafluoro-5-nitrobenzene (3.0 g, 15.4 mmol) and DIEA (3.7 ml, 21.0 mmol) in dry THF (20 ml) was added S-cyclopropyl-l/f-pyrazol-S-amine (1.7 g, 14.0 mmol) in THF (5 ml) drop wise at 0 C. After addition, the reaction mixture was stirred at 25 C for 16 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane-EtOAc = 4 : 1). This was recrystalized from Et2O (20ml) and hexanes (~150ml) to give the title compound as red crystals (0.650 g, 16%). 1H NMR (400 MHz) 11.84 (s, IH), 8.67 (s, IH), 8.06 (m, IH), 5.57 (s, IH), 1.82 (m, IH), 0.89 (m, 2H), 0.65 (m, 2H). MS: Calcd.: 298; Found: [M+H]+ 299.

Statistics shows that 5-Cyclopropyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 175137-46-9.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); A1;,
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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

Example 173 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-4-carboxamide To a solution of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (140 mg, 1.0 mmol) and N,N-dimethylformamide (2 drops) in tetrahydrofuran (10 mL) was added oxalyl chloride (0.171 mL, 2.0 mmol) with stirring under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in N-methylpyrrolidone (5 mL) with stirring under ice-cooling, N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (164 mg, 0.50 mmol) was added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate (80 mL), and washed with 1N aqueous sodium hydroxide solution (10 mL) and water (10 mL*3). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0?70/30) and recrystallized from ethyl acetate to give the title compound (88 mg, yield 39%) as a white solid. melting point 205 C. 1H-NMR (DMSO-d6, 300 MHz) delta 0.73-0.88 (4H, m), 1.86-1.99 (1H, m), 2.32 (3H, s), 3.81 (3H, s), 7.06 (1H, d, J=9.5 Hz), 7.06-7.14 (1H, m), 7.36 (1H, dd, J=10.2, 9.0 Hz), 7.66 (1H, dd, J=6.4, 3.2 Hz), 7.94 (1H, s), 8.03 (1H, d, J=9.5 Hz), 8.32 (1H, s), 9.53 (1H, s), 11.06 (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 78703-53-4.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 78703-53-4, 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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

100 mL with spherical condenserA 1-dimethyl-1H-pyrazole-4-carboxylic acid (7.5 mmol) intermediate was added to a single-necked round bottom flask followed by the addition of 30 mmol of thionyl chloride under stirring. After refluxing for 4 hours, To give 1-methyl-3-methyl-1H-pyrazole-4-acid chloride (V)In step 2), the chlorinating reagent is one or more mixture of thionyl chloride, phosphorus oxychloride or phosphorus trichloride.

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

Reference:
Patent; Zhejiang University of Technology; Liu Xinghai; Zhao Wen; Shen Zhonghua; Peng Weili; Tan Chengxia; Weng Jianquan; (11 pag.)CN106632044; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1572-10-7, 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 1572-10-7 as follows.

General procedure: An oven dried 25 mL RB flaskwas charged with chalcone (1.0 mmol), 3-aminopyrazole (1.2 mmol), KOH (0.1mmol) and DMF (5 mL). The resulting solution was stirred at 110 C for 20 min.On completion, the reaction mass was allowed to cool to ambient temperature,diluted with water (20 mL) and extracted into ethyl acetate (2 20 mL). The combined organic layers were dried overanhydrous Na2SO4, and organic solvent was evaporated on arotatory evaporator. The crude residue was purified by column chromatography(silica gel 60-120 mesh, eluent 20% EtOAc/hexanes).

According to the analysis of related databases, 1572-10-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kaswan, Pinku; Pericherla, Kasiviswanadharaju; Purohit, Deepshikha; Kumar, Anil; Tetrahedron Letters; vol. 56; 3; (2015); p. 549 – 553;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 114474-28-1, 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. 114474-28-1, name is 4-(1H-Pyrazol-4-yl)aniline belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (300 mg, 1.46 mmol), 4-(1H- pyrazol-4-yl)aniline (233, 1.46 mmol), and iPr2NEt (0.51 mL, 2.93 mmol) in DIVIF (2.9 mL) was heated at 100 C for 5h, cooled to rt, and diluted with water. The precipitate formed was collected by filtration and washed with water and dried in vacuo to provide the title compound (470 mg, 98%). MS (ES+) m/e 329 (M+H).

The synthetic route of 4-(1H-Pyrazol-4-yl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 4522-35-4, These common heterocyclic compound, 4522-35-4, name is 3-Iodo-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.

INTERMEDIATE 22 4-(3-Iodo-lH-pyrazol-l-yl -N7V-dimethylpyridin-2-amine To a suspension of 3-iodo-lH-pyrazole (100 mg, 0.516 mmol) and N,N-dimethyl-4- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-amine (1 2 mg, 0.773 mmol), Na2C03 (109 mg, 1.031 mmol) in anhydrous dichloroethane (4 mL) added a suspension of Cu(OAc)2 (94 mg, 0.516 mmol) and 2,2′-bipyridine (81 mg, 0.516 mmol) in dichloroethane (4 mL). The reaction was stirred at 70 C under N2 overnight. The mixture was filtered through the Celite and washed with EtOAc (5 mL x 3), the filtrate was collected and removed in vacuo to give the crude product. This was purified by flash chromatography (ISCO Combiflash, lOg, Biotage Si column, -30 mL/min, 100% hexanes 5 min, gradient to 100% EtOAc in hexanes 15 min) to afford 4-(3-iodo-lH-pyrazol-l-yl)-N,N-dimethylpyridin-2-amine. LCMS calc. = 315.01 ; found = 315.10 (M+H)+.

The synthetic route of 4522-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 31037-02-2, name is Ethyl 5-amino-1-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. category: pyrazoles-derivatives

A solution of ethyl 5-amino-1-methyl-4-pyrazole carboxylate (42.2 g, 0.25 mol) in THF is treated with NaH (60% in mineral oil, 25.2 g, 0.75 mol), stirred for 30 min, treated with ethyl 3-methoxy-3-[(trifluoromethyl)phenyl]-2-propenoate (65.5 g, 0.25 mol), heated at reflux temperature for 36 h, cooled to 0 C., acidified to pH 5 with aqueous HCl and extracted with EtOAc. The extracts are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. The resultant off-white solid residue is triturated with hexanes to give a white solid. The solid is dissolved in phosphorus oxychloride (750 mL) and heated to reflux temperature for 2 h, cooled to room temperature and concentrated. This concentrate is dissolved in EtOAc, cooled to 0 C., and neutralized with aqueous Na2CO3. The organic phase is separated, washed with brine, dried over Na2SO4 and concentrated. This resultant residue is chromatographed on silica gel (3:1 hexanes:EtOAc) to afford the title compound as a white solid 65% (68% yield), characterized by H-NMR and mass spectral analyses.

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

Reference:
Patent; Wyeth; US2004/24008; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics