Category: 641571-11-1

Reference of 641571-11-1, 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. 641571-11-1 name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

Example 2; Recrystallization of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I from IPA/waterA 50 mL flask was charged with 1 g of the compound of Formula I crude (purity of 82.5%) and 3.5 mL of IPA. The mixture was heated to 45 C. under stirring until the entire solid dissolved. At 45 C., 6 mL of water was added drop-wise. The mixture was stirred for 10 min and cooled slowly to 010 C. The mixture was stirred at 010 C. for 10 min and filtered to obtain the recrystallized compound of Formula I having a purity of 98%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); 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., Application In Synthesis of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Example 1[51] Synthesis of 4-methyl-N-[3-(4-methylimidazole-l-yl)-5-trifluoromethyl-phenyl] -3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzamide [52][53] Method A[54] In a reactor, potassium tert-butoxide (20.9g, 186.56mmol) was dissolved in tetrahydrofuran (167ml), and then was cooled to -20+50C. To the resultant product, 3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) dissolved in tetrahydrofuran (80ml) was added and stirred for 30 minutes. When the stirring was completed, 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester (15.5g, 45.60mmol) dissolved in tetrahydrofuran (90ml) was slowly added to the resultant product. After the addition, the temperature of the mixture was slowly elevated to room temperature, and stirring was carried out until the reaction was completed. When the reaction was completed, the reaction mixture was cooled to 5-1O0C, and then 15% sodium chloride aqueous solution (337ml) was slowly added to the reaction mixture. After the addition, the temperature of the reaction mixture was slowly elevated to room temperature again, and then water (170ml) was added thereto and an organic layer was extracted and separated.[55] To the organic layer, ethyl acetate (400ml) was added. Then, the layer was washed with water (200ml), separated and was subjected to vacuum concentration. When the concentration was completed, methanol (220ml) was added thereto. Then, the resultant layer was subjected to reflux- stirring for 1 hour, cooled to room temperature, and then stirred for 2 hours.[56] The obtained solid was filtered, sufficiently washed with methanol (100ml), and then dried to provide a pale yellow solid final compound (17.51g, yield 81%).[57] 1H-NMR(DMSOd6, delta= 2.19(s,3H), 2.36(s,3H), 7.24(s,lH), 7.35(m,2H), 7.47 (s,lH),7.64(d,lH), 7.71(d,lH), 7.92(d,lH), 8.01(s,lH), 8.11(s,lH), 8.30(s,2H), 8.47(d,lH), 9.00(s, IH), 10.49(s,lH)

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

Reference:
Patent; IL-YANG PHARM. CO., LTD.; KIM, Dong Yeon; CHO, Dae Jin; LEE, Gong Yeal; KIM, Hong Youb; WOO, Seok Hun; WO2010/18895; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, 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 641571-11-1 as follows.

4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (100 g, 0.326 mole) and 5-(4-methyl- IH-imidazol-1-yl)-3-(trifluoromethyl)benzenamine (78.75 g, 0.326 mole) were stirred in N-methyl pyrrolidone (700 ml) at 55-60C. Thionyl chloride (83 ml, 0.978 mole) was added and the temperature of the reaction mass was raised to 75C and stirred for 6 hours. The reaction masswas cooled to 40-45C, and water (500 ml) was added. The reaction mass was cooled to 20-25C and acetone (3000 ml) was added. The reaction mass was further stirred for 12 hours. The solid was isolated by filtration and washed with acetone to obtain nilotinib base.Yield :- 200 g

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CIPLA LIMITED; KING, Lawrence; RAO, Dharmaraj Ramachandra; MALHOTRA, Geena; PATHI, Srinivas Laxminarayan; CHINIMILLI, Venugopalarao; GANGRADE, Manish Gopaldas; (21 pag.)WO2016/151304; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, 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 641571-11-1 as follows.

Method II; To a flask was added 6-methyl-5-[4-(pyrid-3-yl)pyrimid-2-ylamino) nicotinic acid (30.7 g) and SOCl2 (500 mL) and the reaction mixture was refluxed for 4 hours. The reaction mixture was concentrated under reduced pressure to give a solid, which is used for the next step directly. To the above acid chloride was added a clear solution of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (24.1 g) in pyridine (200 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and then the residue was added with chloroform (500 mL) and water (500 mL) and extracted. The organic phase was dried, filtrated, concentrated, and purified through column chromatography to give the titled compound.

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun, Piaoyang; EP1840122; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

0 ~ 5 ,A solution of 3- (4-methyl-1H-1-imidazolyl) -5-trifluoromethylaniline (24.1 g, 0.1 mol)Acetyl chloride (11.7 g, 0.15 mol) and dichloromethane (150 mL) were added to a three-necked reaction flask,Triethylamine (15.0 g, 0.15 mol) was added dropwise with stirring,After that,Heating up to 25 ~ 35 ,Reaction for 2 hours,TLC detection, to the raw material reaction completely.The reaction solution was poured into ice water, and the layers were allowed to stand. The aqueous phase was extracted with methylene chloride, the organic phase was combined, washed with 10% sodium hydrogencarbonate solution, dried, the solvent was removed under reduced pressure,Get like white solidN- [3- (4-methyl-1H-1-imidazolyl) -5-trifluoromethylbenzene] acetamide (III)(Acetyl-protected compound of formula II)

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

Reference:
Patent; Suzhou Lixin Pharmaceutical Co., Ltd.; Xu Xuenong; Bao Zhijian; Su Jian; Xue Jia; Gu Xinyu; Huang Dongliang; Chen Wei; Wang Zhe; (6 pag.)CN107188887; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 641571-11-1, 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. 641571-11-1 name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

A three-necked 250 mL round bottom flask equipped with thermometer, condenser, and stir bar, was charged with toluene (75 mL), ethyl 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoate (3 g, 9.0 mmol, 1 eq.), and 5-(4-methyl)-1H-imidazol-1-yl)-3-(trifluoromethyl)benzenamine (2.82 g, 11.7 mmol, 1.3 eq.). The suspension was warmed up and 6.8 mL AlMe3 (2 M in toluene, 13.8 mmol, 1.5 eq.) was added. The entire mixture was then being refluxed for 5 hrs until the ester disappeared and the process was monitored by an HPLC. After the mixture was cooled down, excess trimethyl aluminum was quenched with aqueous sodium hydroxide. The product was isolated by filtration and dried under vacuum affording 4.32 g (91%) nilotinib with 99.3% purity (HPLC). Results of other examples with different ratio of starting material are listed in the Table 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; FORMOSA LABORATORIES, INC.; Hung, Jui-Te; Chen, Wen-Chin; US9187452; (2015); B1;,
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., Recommanded Product: 641571-11-1

A mixture of 46 (100 mg, 0.39 mmoi) and LiOH (28 mg, 1.17 mmoi) in THF/H20 (2/1 mL) was stirred at room temperature for 8 hours. TLC indicated the reaction was compiete. The reaction mixture was diiuted with water and acidified to pH 3 with aqueous HCi. The resuiting precipitate was fiitered washed with water and dried to give 47 (90 mg, 95%) as a white soiid. To a soiution of 47 (100 mg, 0.41 mmoi) in NMP (1 .5mL) was added SOCi2 (74 mg, 0.62 mmoi). The reaction was heated at 60 C for 1 hour before 3 (100 mg, 0.41 mmoi) and Et3N (166 mg, 1 .64 mmoi) were added. The resuiting mixture was stirred at 60 C for 3 hours. The reaction was directiy purified by reverse prep-H PLC and then siiica gei prep-TLC to give 3-(benzyioxy)-4-methyi-N-(3-(4-methyi- 1 H-imidazoi-1 -yi)-5-(trifiuoromethyi)phenyi)benzamide (25 mg, 13%) as a white soiid.

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

Electric Literature 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.

To a solution of 2- (4-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-methylpyrimidine-5-carboxylic acid (0.2 g 0.506 mmol) in 1 4-dioxane (3 mL) stirred under N2at 20 was added Et3N (0.106 mL 0.759 mmol) and DPPA (0.167 g 0.607 mmol) in one charge. The reaction mixture was stirred at rt for 30 mins. To the mixture a solution of 3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) aniline (0.122 g 0.506 mmol) in 1 mL of 1 4-dioxane was added. The reaction solution was heated to 100 with stirring for 3 hr. The solution was concentrated in vacuo and the residue was purified by preparative TLC (DCM/MeOH 101 Rf 0.5) to yield a off white solid of 1- (2- (4-ethoxy-6- ( (4-methoxybenzyl) oxy) pyridin-3-yl) -4-methylpyrimidin-5-yl) -3- (3- (4-methyl-1H-imidazol-1-yl) -5- (trifluoromethyl) phenyl) urea (60 mg 0.095 mmol 18.7yield) 1HNMR(400 MHz CD3OD) delta9.18 (s 1H) 9.15 (s 1H) 8.39 (s 1H) 8.25 (s 1H) 8.04 (s 1H) 7.81 (s 1H) 7.54 (s 1H) 7.25-7.23 (m 2H) 6.87-6.85 (m 2H) 6.48 (s 1H) 5.31 (s 2H) 4.13-4.10 (m 2H) 3.79 (s 3H) 2.82 (s 3H) 2.59 (s 3H) 1.40-1.36 (m 3H) ES-LCMS m/z 634.2 (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-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Related Products 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.

Method D[98] A pale yellow solid final compound (15.3g, yield 71%) was obtained by reacting3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) with 3-(4-imidazole-l-yl-pyrimidine-2-yl amino)-4-methyl-benzoic acid phenyl ester in a similar manner as described in Method A of Example 1, except that 3-(4-imidazole-l-yl-pyrimidine-2-yl amino)-4-methyl-benzoic acid phenyl ester (16.9g, 45.60mmol) was used, instead of 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester.

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

Adding a certain compound to certain chemical reactions, such as: 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, belongs to imidazoles-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 641571-11-1, Computed Properties of C11H10F3N3

To a solution of 3-(4-methylimidazol-l-yl)-5-(trifluoromethyl)aniline (0.7 equiv, prepared according to literature known methods) in THF under nitrogen atmosphere was added 3-Iodo-4-methyl benzoyl chloride (1 equiv, prepared from the reaction of 3-iodo-4- methylbenzoic acid and SOCl2) in THF at room temperature during 30minutes followed by drop wise addition of (i-Pr)2EtN (2 equiv) and 4-DMAP (0.2 equiv). After stirring at ambient temperature over 3h, the reaction mixture was quenched with water. The resulting mixture was stirred at 0-5C for 60min. Compound was collected by filtration. This compound was further purified by silica gel chromatography (eluted with 2% methanol/ chloroform) to provide the title compound (85% yield). ESI MS m/z – 486.2 (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-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.