Category: 33468-69-8

33468-69-8, Adding some certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8.

To 100 mg (0.36 mmol) of (S)-5-(4-fluoro-3-(trifluoromethyl)phenyl)-6-methyl-3,6-dihydro- 2H-1,3,4-oxadiazin-2-one (Intermediate 75) and 73 mg of 4-trifluoromethyl imidazole (0.54 mmol) dissolved in 2 mL of DMF was added 235 mg of powdered Cs2C03 (0.72 mmol) and the mixture was heated at 80 Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSTITUTE, INC.; ELLERMANN, Manuel; GRADL, Stefan, Nikolaus; KOPITZ, Charlotte, Christine; LANGE, Martin; TERSTEEGEN, Adrian; LIENAU, Philip; HEGELE-HARTUNG, Christa; SUeLZLE, Detlev; LEWIS, Timothy, A.; GREULICH, Heidi; WU, Xiaoyun; MEYERSON, Matthew; BURGIN, Alex; (500 pag.)WO2019/25562; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8, 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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.18 g of 4-(trifluoromethyl)-lH-imidazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.40 g of 2- { 3- [4-(trifluoromethyl)imidazole- 1 -yl]pyridin-4-yl } -5 -(trifluoromethyl)benzoxazole hereinafter, referred to as “active compound 57”).Active compound 57-NMR (CDC13) delta: 9.00 (d, J=5.2 Hz, 1H), 8.84 (s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8.06-8.04 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.70 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.52-7.50 (m, 1H)

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49221; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8, Recommanded Product: 33468-69-8

Production Example 58A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.18 g of 4-(trifluoromethyl)-lH-imidazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.40 g of 2-{3-[4-(trifluoromethyl)imidazole-l-yl]pyridin-4-yl}-5-(trifluoromethyl)benzoxazole hereinafter, referred to as “active compound 57”).Active compound 571H-NMR (CDC13) delta: 9.00 (d, J=5.2 Hz, 1H), 8.84 (s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8.06-8.04 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.70 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.52-7.50 (m, 1H)

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, 4-(Trifluoromethyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49222; (2011); 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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 33468-69-8

Referring to Reaction Scheme 14, Stage 1, a solution of 4-chloro-6-(3,4- dichloro-phenyl)-pyrimidine (1eq), 4-(trifluoromethyl)-1H-imidazole (2eq) and potassium carbonate (1.1eq) in fert-butanol (10vol) was heated at 150C in a microwave for 25 minutes. Potassium carbonate (1.1eq) was added to the reaction mixture, which was heated at 160C in a microwave for 35 minutes. Water was added and the desired material was extracted with EtOAc. The organic phase was dried with MgSO4, filtered and evaporated to dryness. Purification by flash column chromatography (eluent: [99.5:0.5] DCM:MeOH) afforded the target compound.

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOMINGUEZ, Celia; TOLEDO-SHERMAN, Leticia, M.; COURTNEY, Stephen, Martin; PRIME, Michael; MITCHELL, William; BROWN, Christopher, John; DE AGUIAR PENA, Paula, C.; JOHNSON, Peter; WO2013/16488; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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 33468-69-8, SDS of cas: 33468-69-8

Example 5: Preparation of Compound 25A microwave vial was charged with Intermediate F (20 mg, 0.044 mmol), 4-(trifluoromethyl)- lH-imidazole (20 mg, 0.15 mmol), CS2CO3 (43.2 mg, 0.133 mmol) and DMA (500 mu). The mixture was heated at 150C under microwave irradiation for 3 h. The mixture was then purified by reverse-phase preparative HPLC (0: 100 to 95 :5 MeCN:water: 0.1% v/v TFA modifier) to afford 1-25 as the TFA salt. ‘H NMR (500 MHz, DMSO-d6) delta = 8.68-8.20 (m, 4H), 5.00 (s, 1H), 4.55-4.38 (m, 1H), 4.22-4.16 (m, 1H), 4.12 (q, 3=1 A, 2H), 3.35-3.24 (m, 1H), 3.22-3.01 (m, 2H), 2.33-2.21 (m, 1H), 2.21-2.09 (m, 1H), 1.30 (d, /=6.9, 5H), 1.24 (t, /=7.2, 3H). MS (EI) Calc’d for C20H24F3N10 [M+H]+, 461; found 461.

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; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; FONG, Kin Chiu; ANTHONY, Neville John; ZHOU, Hua; KATZ, Jason D.; YANG, Lihu; LI, Chaomin; TIAN, Yuan; MU, Changwei (Charles); YE, Baijun; SHI, Feng; ZHAO, Xiaoli; FU, Jianmin; WO2015/188369; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

Ten (10) mL of a 36% aqueous solution of formaldehyde was added to a solution containing 1.00 g of A- trifluoromethylimidazole and 0.4 mL of a 10% tetra-n- butylammonium hydroxide solution in 10 mL of tetrahydrofuranat room temperature. The mixture was stirred at the same temperature for 14 hours and then concentrated under reduced pressure. The resultant residue was subjected to column chromatography to obtain crude 4- trifluoromethylimidazol-1-ylmethanol . The crude product was dissolved in 20 mL of chloroform and thereto 0.8 mL of thionyl chloride was added at room temperature. The mixture was stirred under reflux conditions for 16 hours, allowed to be cooled to room temperature, and then concentrated under reduced pressure. The resultant residue was dissolved in 20 mL of tetrahydrofuran and thereto 940 mg of S- (3, 3, 3-trifluoropropyl) benzenethioate was added. To the solution, 2.4 mL of a 28% solution of sodium methoxide in methanol was added dropwise at room temperature. After stirring at the same temperature for 10 hours, to the reaction mixture was added 10% hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to column chromatography to obtain 800 mg of 4-trifluoromethyl-1- [ (3, 3, 3- trifluoropropylsulfanyl) methyl] -lH-imidazole (hereinafter referred to as the present compound (3)) . The present compound (3) : 1H-NMR (CDCl3, TMS): delta (ppm) 7.65 (IH, s), 7.43 (IH, s), 5.01 (2H, s), 2.67-2.71 (2H, m) , 2.27-2.381 (2H, m) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethyl)-1H-imidazole, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/28727; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 33468-69-8, 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 33468-69-8 as follows.

Sodium hydride (7.91 mg, 0.198 mmol, 60% in mineral oil) was added to a solution of 4- (trifluoromethyl)-I H-imidazole (24.46 mg, 0.180 mmol) in dry N,N-dimethylformamide (0.4 ml). The reaction was stirred at room temperature for 30 minutes until gas evolution ceased. A solution of 2-(5- bromo-4-methyl-1 ,2,4-triazol-3-yl)-3-ethylsulfanyl-5-(trifluoromethyl)pyridine (66.0 mg, 0.180 mmol) in N,N-dimethylformamide (2.0 ml) was slowly added and the reaction mixture stirred at room (0511) temperature for 30 minutes. Two more equivalents of the previously described solution consisting of sodium hydride and 4-(trifluoromethyl)-1 H-imidazole were then added and stirring continued overnight at 60C. The mixture was quenched over water and ethyl acetate, the layers separated, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (cyclohexane/ethyl acetate) to afford 3-ethylsulfanyl-2-[4-methyl-5-[4-(trifluoromethyl)imidazol-1-yl]-1 ,2,4-triazol-3-yl]-5- (trifluoromethyl)pyridine (compound P2) as a solid (55 mg). LCMS (method 4): 423 (M+H)+, retention time 0.97 min. H-NMR (CDCb, ppm) 8.70 (t, 1 H), 8.00 (d, 1 H), 7.94 (d, 1 H), 7.71 (m, 1 H), 3.81 (s, 3H), 3.06 (q, 2H), 1.42 (t, 3H).

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; MUEHLEBACH, Michel; EDMUNDS, Andrew; RENOLD, Peter; BUCHHOLZ, Anke; (96 pag.)WO2018/41729; (2018); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

[00611] Intermediate 64a: benzyl 2-[4-(trifluoromethyl)imidazol-1 -yI]acetate[00612] Benzyl bromoacetate (0.l4mL, 0.88mmol) was added to a flask containing potassiumcarbonate (305mg, 2.2mmol) and 4-(trifluoromethyl)-1H-imidazole (1 00mg, 0.73mmol) in MeCN(3mL). The reaction mixture was heated to 60 C and left to stir overnight. The reaction was then quenched by the addition of water (2OmL) and extracted with EtOAc(3x2OmL). The combined organic layers were dried over Na2504, filtered and reduced in vacuo to afford the product benzyl 2- [4-(trifluoromethyl)imidazol-1-yl]acetate (1 94mg, 0.68mmol, 93% yield) as a yellow oil.1H NMR (CDCI3,400MHZ) O/ppm: 7.55 (1H, 5), 7.41 -7.30 (6H, m), 5.23 (2H, 5), 4.75 (2H, 5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethyl)-1H-imidazole, its application will become more common.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, 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. Computed Properties of C4H3F3N2

To a 0 C. solution of 4-(trifluoromethyl)-1H-imidazole (1.82 g, 13.4 mmol) in DMF (20 mL) was added sodium hydride (0.81 g, 20.1 mmol). The mixture was stirred at room temperature for 1 h. The crude 2,6-dimethyl-4-nitrophenyl trifluoromethanesulfonate prepared above (4.0 g, 13.4 mmol) was added. The mixture was stirred at 80 C. for 12 h. The reaction was diluted with water and extracted with ethyl acetate (30 mL*3). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give 1-(2,6-dimethyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazole (805 mg, 21%) as a colorless solid. 1H NMR (400 MHz, CDCl3) delta 8.01 (s, 2H), 7.47 (s, 1H), 7.23 (s, 1H), 2.11 (s, 6H).

The synthetic route of 33468-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; US2012/202834; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8,Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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.

Sodium hydride (60% in mineral oil; 0.4 g, 10 mmol) was added portionwise to a stirred solution of 4-(trifluoromethyl)-lH-imidazole (1.15 g, 8.45 mmol) in THF (19 mL) at 0 C. After stirring at 0 C for 30 minutes 2-(trimethylsilyl)ethoxymethyl chloride (1.69 g, 10 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. Water was added and the product extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated in vacuo to yield 4-(trifluoromethyl)-l-{[2-(trimethylsilyl)ethoxy]methyl}- lH-imidazole (2.2 g, 98 % yield) that was used in the next step without further purification.

The synthetic route of 33468-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; TRABANCO-SUAREZ, Andres, Avelino; DELGADO-JIMENEZ, Francisca; VEGA RAMIRO, Juan, Antonio; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; OEHLRICH, Daniel; WO2012/85038; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem