Category: 641571-11-1

Synthetic Route of 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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 12; Preparation of NilotinibTo 1 L glass reactor was added the compound of formula 4-methyl-3-{[4-(pyridin-3-yl) pyrimidin-2-yl]amino}benzoic acid of formula X (80.0 g, 0.26 mol), and N-Methyl-pyrrolidone (400 mL). The mixture was heated to 60 C., then SOCl2 (24 mL, 0.33 mol) was added during 15 minutes. The resulted mixture was stirred at 60 C. for 1 h. A compound of formula I (69.2 g, 0.29 mol) was added and the reaction mixture was stirred and heated to 90 C. for 3 h. Water (500 mL) was added and the solution was heated to 80 C. NaOH 47% solution (65 mL) was added until pH 11-12. Then, the suspension was cooled to 40 C. and stirred at this temperature for 2 hours, filtered under reduced pressure at 40 C., and washed with 500 mL H2O to yield a beige solid. This material was slurried in water (1 L) at 40 C. for 1 h, filtered, washed with water (500 mL), and dried under vacuum at 50 C. to obtain 135.25 g of Nilotinib base with 94% yield. (95.8% assay, 99.46% purity).

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, The chemical industry reduces the impact on the environment during synthesis 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life.

To a solution of 7 (100 mg, 0.33 mmol) in NMP (2 mL) was added SOd2 (58 mg,0.49 mmol). The reaction was heated at 90 C for 1 hour before 3 (80 mg, 0.33 mmol)was added. The resulting mixture was stirred at 90 C for 3 hours. The reaction was quenched with water and basified with aqueous NaOH. The mixture was extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give 4-methyl-N-(3-(4-methyl-1 H-imidazol-1 -yl)-5-(trifluoromethyl)phenyl)-3-((4-(pyridin-2-yl)pyrimidin-2-yl)amino)benzamide (23 mg, 13%) as a gray solid.

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-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of chloroanhydride in dry CHCl3 was addedamine R2NH2 (one equivalent) and Et3N (1.5 equivalents). The reaction mixture was stirred atroom temperature. The reaction progress was monitored by TLC. Cold water was added to thereaction mixture. The organic layer was separated from the water. The combined organic layers weredried over Na2SO4, filtered, and concentrated under vacuum. The product was purified by columnchromatography on silica gel.

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-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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 641571-11-1

A solution of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline(524 mg, 2.0 mmol) and Et3N (10 mmol) in anhydrous THF (6 mL) wascooled to 0 C in an ice bath. The light yellow solution preparedbefore was then added dropwise. The mixture was allowed to warm toroom temperatureand maintained for 1 h. The reaction mixture was quenched by addition of saturatedNaCl solution and the reaction mixture was extracted several times with EtOAc.Thecombined organic extracts were dried with Na2SO4,filtered, and concentrated in vacuo. The resultant crudematerial was purifiedby column chromatography to give the title compound 7 (873 mg, yield 90% of two steps). 1H NMR (400 MHz, DMSO-d6) d 10.80 (s, 1H), 8.66 (s, 1H),8.47 (d, J = 1.6 Hz, 1H), 8.39 (s, 1H), 8.19 (s, 1H), 7.98 (dd, J = 1.6, 8.0Hz, 1H), 7.79 (s, 1H), 7.66 (s, 1H), 7.53 (d, J = 8.0 Hz ,1H), 2.46 (s, 3H),2.24 (s, 3H). LC-MS (ESI):m/z 486 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 641571-11-1, its application will become more common.

Reference:
Article; Lu, Xiaoyun; Zhang, Zhang; Ren, Xiaomei; Pan, Xiaofeng; Wang, Deping; Zhuang, Xiaoxi; Luo, Jingfeng; Yu, Rongmin; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3458 – 3463;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, These common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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: A mixture of acid 7b (or 7c) (1.3 equivalents), 1-hydroxybenzotriazole (1.3 equivalents), andN,N?-dicyclohexylcarbodiimide or 1,1?-carbonyldiimidazole (1.3 equivalents) was dissolved in dryDMF. Et3N (2.5 equivalents) and amine R2NH2 (one equivalent) were added. The resulting mixture was stirred at room temperature. The reaction progress was monitored by TLC. The solvent wasremoved under reduced pressure. The crude was diluted with water, and NH4OH was added to obtainpH = 10-11. The resulting solid was filtered and washed with water. The product was purified bycolumn chromatography on silica gel.

Statistics shows that 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 641571-11-1.

Reference:
Article; Kalinichenko, Elena; Faryna, Aliaksandr; Kondrateva, Viktoria; Vlasova, Alena; Shevchenko, Valentina; Melnik, Alla; Avdoshko, Olga; Belko, Alla; Molecules; vol. 24; 19; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

To 400 mL of N-methyl-2-pyrrolidone, 80.0 g (261 mmol) of compound [1] and 0.43 g (5.2 mmol) of cyclohexene were added, and 43.5 g (366 mmol) of thionyl chloride was added dropwise at 20 to 40 C., followed by 60 C. The temperature was raised and the reaction was carried out for 1 hour. After confirming the reaction end point, a solution prepared by dissolving 63.0 g (261 mmol) of compound [3] in 400 mL of N-methyl-2-pyrrolidone was added dropwise to the reaction mass, and the mixture was reacted at 60 C. for 3 hours. After 400 mL of water was introduced into the reaction mass, the temperature was raised to 80 C, 83.0 g of a 20% KOH aqueous solution was added dropwise, and the temperature was kept at 80 C for 3 hours or more.Subsequently, 112.3 g of a 20% KOH aqueous solution was added dropwise over 1 h. After cooling to 60 C., 45.2 g of a 40% K 2 CO 3 aqueous solution was added dropwise, and the mixture was cooled to 40 C. over about 2 hours. The obtained crystals were dried under reduced pressure to obtain 128.6 g of compound [4] (nilotinib) (yield 93.0%). The area percentage of the peak of the target substance in the LC chromatogram was 99.96% (nuclear chlorinated product was not detected).

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; Sumitomo Chemical Co., Ltd.; Kumazawa, Hiroharu; Akiyama, Masaki; (8 pag.)JP2020/7240; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-Iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)Benzamide: 3-Iodo-4-methylbenzoic acid (2.62 g, 10 mmol) was refluxed in soc2 (10 mL) for 5 1 h. The volatile components were removed on a rotavap and the residue was dissolved inbenzene (10 mL), concentrated to dryness on a rotavap and further dried under vacuum. The resulting acyl chloride was added to a solution 3-(4-methyl-IH-imidazol-I-yl)-5- (trifluoromethyl)benzenearnine (2.46 g, 10.2 mmol), N,N-diisopropylethylamine (1.56 g, 12 mmol), and a catalytic amount of DMAP in THF (20 mL). After stirring at rt for 2 h, the reaction10 was quenched with water. EtOAc was added and the layers separated. The combined organic layers were concentrated to dryness and used without purification in next step.

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

641571-11-1, 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1006361 A solution of 3 -((4-(5-methoxypyridin-3 -yl)pyrimidin-2-yl)amino)-4-methylbenzoic acid (6.4 g, 19.02 mmol) in NMP (64 mL) was dropwise charged with thionylchloride (2.7 g, 22.8 mmol) at room temperature and heated to 60 C for 1 h. The solution wascharged with 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (5.5 g, 22.8 mmol) andheated to 90 C for 3 h. The reaction mixture was diluted with water (120 mL), adjusted pH to10 with 40% aqueous sodium hydroxide solution and stirred at 80 C for 30 mm. The reactionmixture was cooled to 40 C and the solid precipitated out was filtered and washed with water.The residue obtained was again stirred in water at 40 C for 1 h and solid was filtered and driedto give 5.60 g, 52% yield of the title compound as a white solid. ?H NMR (400 MHz, DMSO-= 10.61 (s, 1 H), 9.16 (s, 1 H), 8.88 (d, J= 1.34 Hz, 1 H), 8.56 (d, J= 4.91 Hz, 1 H), 8.36- 8.42 (m, 2 H), 8.28 (s, 1 H), 8.15 -8.21 (m, 2 H), 7.95 -8.00 (m, 1 H), 7.69-7.79 (m, 2 H),7.52 (d, J= 5.35 Hz, 1 H), 7.41 -7.50 (m, 2 H), 3.83 (s, 3 H), 2.37 (s, 3 H), 2.18 (s, 3 H); MS(ES): m/z = 560.30 [M+H] LCMS: tR = 2.61 mm.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COFERON, INC.; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/106292; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., 641571-11-1

To a solution of 2- (5-ethoxy-6-oxo-1 6-dihydropyridin-3-yl) -4 6-dimethylpyrimidine-5-carboxylic acid (150 mg 0.519 mmol) 3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) aniline (125 mg 0.519 mmol) and Et3N (79 mg 0.778 mmol) in 1 4-dioxane (5 mL) stirred under N2at 20 was added DPPA (171 mg 0.622 mmol) in one charge. The reaction mixture was heated to 80 for 1 hr. Then the solution was concentrated. The residue was purified by preparative HPLC (Instrument DC/Column ASB C18 150*25mm/Mobile phase A Water+0.1HCl/Mobile phase BMeCN /Flowrate 25 mL/min /Gradient Profile Description 15-55 (B) ) to yield a off white solid of 1- (2- (5-ethoxy-6-oxo-1 6-dihydropyridin-3-yl) -4 6-dimethylpyrimidin-5-yl) -3- (3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) phenyl) urea dihydrochloride (11.53 mg 3.67) . TLC (DCM/MeOH 51 Rf 0.4) 1HNMR(400 MHz CD3OD) delta9.44-9.40 (m 1H) 8.27-8.23 (m 1H) 8.20 (s 1H) 7.92 (s 2H) 7.84 (s 1H) 7.69 (s 1H) 4.17 (d J 6.8 Hz 2H) 2.57 (s 6H) 2.44 (s 3H) 1.48 (t J 6.9 Hz 3H) ES-LCMS m/z 528.2 (M+H)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., 641571-11-1

Example 31[00105] Form B of the free base of 4-methyl-N-[3-(4-methyl-imidazol-l-yl)-5- trifluoromethyl-phenyl] -3 -(4-pyridin-3 -yl-pyrimidin-2-ylamino)-benzamide is made according to the following scheme: EPO Eq.)10 [00106] 14.5 g (60.0 mmol) of B6 and 20.8 g (64.8 mmol) of B5 are dissolved in 120 niL tetrahydrofuran absolute at room temperature under inert and water-free conditions. The suspension is cooled to IT 0-5C and 101.0 g (180 mmol) of potassium tert-butoxide solution 20% in tetrahydrofuran were added within 1 hour, maintaining the internal temperature at 0-5C. The reaction mixture is heated gradually to IT 50C within 1 hour and then stirred at this temperature for another 1 hour. The reaction mixture (yellow suspension) is quenched at IT 5O0C by the addition of 50 mL of water. Stirring is stopped, and the two phase system is let to separate. The aqueous (lower) phase is removed. Approximately 1.0 mL of acetic acid is added to the organic phase until a pH of ~10 is reached. Seeding crystals (0.2 g) of form B are added to the organic solution. Solvent (260 mL) is distilled off at 80-100C (external temperature) under normal pressure, and simultaneously 260 mL ethanol 94% is added keeping the volume constant, i.e., solvent exchange from tetrahydrofuran to ethanol. The suspension is cooled to IT 0-5C within 1 hour, and agitation is continued for another 1 hour. Form B of the free base of 4-methyl-N-[3-(4-methyl-imidazol-l-yl)-5-trifluoromethyl- phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide (crystalline solid) is collected by filtration and washed with 150 mL of cold ethanol 94%. The product is then dried at 50C in vacuo.

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; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2007/15870; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem