Category: 1546-79-8

Application of 1546-79-8, 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. 1546-79-8 name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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.

I -(‘rrifliioroacetyl)iniida ole (37.7 p.L, 331 mueta,iotaomicronIota, 6.00 equiv) was added dropwise to a solution of I2-p ~mutilm 94 (17.7 mg. 55.2 mutauetaomicron, 1 equiv) in ethyl acetate (1.0 mL) at -78 C. The resulting mature was stirred for 50 mm a -78 C. The product mixture was diluted with aqueous hydrochloric acid solution (1 , 200 pL) and then was wai’med to 22 C over 1 h. The warmed product .mixture was diluted with aqueous hydrochloric acid solution (.1 M, 1. mL), The diluted product mixture was extracted with ethyl acetate (3 x 5 mL). The organic layers were combined and the combined organic layers were dried over sodiam sulfate. The dried solution was filtered and the. filtrate was concentrated. The residue obtained was purified by preparative thiii-layered chromatography (elutiog with 40% ether-pentaue) to provide the ester S16 as a white solid (15.0 mg, 65%). Rf~ 0.65 (40% ether-pentane, PAA stains purple) H NMR (500 MHz, CDCU) 5.62 (dd, ./= 17.4, 10.8 Hz, 1 H), 5.12-4.98 (m, 3H), 4,39-4.33 (m, IH), 2.53 (p, J – 7.2 Hz, 1H), 2.38-2.03 (m, 4H), 1.82-L66 (m, 3H), 1.60-1.40 (m, 3H), 1.38 (s, 3H 1 -33 (s, 3H), 1.29-1.13 (m, 2H), 0.99 (d, J = 7.1 Hz, 3H 0.83 (d, J = 7.1 Hz, Ml } 5SF NMR (470 MBzs CD?)?-75.09 (s, 3F). ,3C NMR (151 MHz, CDC ) 216.8, 156.8 (q, / – 42.0 Hz), 145,0, 1 14.8 (q, J~ 286.1 Hz), 1 14.0, 80.1, 66.4, 59.2, 46.0, 45.2, 43.8, 42.7, 36.9, 34.9, 34.5, 30.4, 27.3, 25.3, 183, 15.0, 13,5, 1 1 ,6. HRMS-ESI (m/z): calculated for [C22- FjOjN ]”*’ 439.2067, found 439.2046.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; YALE UNIVERSITY; HERZON, Seth; MURPHY, Stephen, K.; ZENG, Mingshuo; (194 pag.)WO2018/144717; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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. COA of Formula: C5H3F3N2O

General procedure: The compound 6b (35.1 mg, 50 mumol) was dried by repeated coevaporations with dry MeCN (3 mL) under Ar. The thymidine 3?-O-oxazaphospholidine derivative 7t (75.5 mg, 0.10 mmol), which was dried in vacuo overnight, and a 0.3 M solution of CMPT 8 (0.5 mL), which was dried over MS3A overnight, were successively added, and the mixture was stirred for 20 min at rt under Ar. N-(Trifluoroacetyl)imidazole (17.0 muL, 0.15 mmol) and i-Pr2NEt (44.0 muL, 0.25 mmol) were added and the mixture was stirred for 30 min at rt. Then DTD (31.9 mg, 0.15 mmol) was added and the mixture was stirred for 50 min at rt. The mixture was then concentrated under reduced pressure, and the residue was dissolved in dichloromethane (5.0 mL). A 6 vol% DCA solution in dichloromethane (5.0 mL) and Et3SiH (1.2 mL, 7.5 mmol) were added and the mixture was stirred for 20 min at rt. The mixture was washed with saturated NaHCO3 aqueous solutions (3 ¡Á 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 ¡Á 10 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by FSPE [1.6 cm column id, 4.8 g of fluorous silica gel, methanol-H2O 16 mL (80:20, v/v) then THF 25 mL] to give 14t, a, c or g as a colorless foam, which was analyzed by 31P NMR (Fig. 2). The 14t, a, c or g thus obtained was dissolved in ethanol (8.0 mL) and a 25% NH3 aqueous solution (40 mL) was added. The mixture was put in a sealed flask and heated at 55 C for 12 h while stirring. The mixture was then cooled to rt, concentrated under reduced pressure to ca. 20 mL The mixture was diluted with a 0.1 M ammonium acetate buffer (pH 7.0) (20 mL) and washed with CHCl3 (4 ¡Á 20 mL). The aqueous layer was then concentrated under reduced pressure. The residue was repeatedly lyophilized from distilled H2O to remove ammonium acetate to give crude the dinucleoside phosphorothioate (15t, a, c or g), which was analyzed by RP-HPLC [Senshu Pak PEGASIL ODS, 4 ¡Á 150 mm, linear gradient of 0-20% MeCN (60 min) in 0.1 M triethylammonium acetate buffer (pH 7.0), 50 C, 0.5 mL/min]. Authentic samples of 15t,a,c,g were synthesized via the solid-phase synthesis using the nucleoside 3?-O-oxazaphospholidines 7t,a,c,g as monomer units [8d].

The synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Oka, Natsuhisa; Murakami, Ryosuke; Kondo, Tomoaki; Wada, Takeshi; Journal of Fluorine Chemistry; vol. 150; (2013); p. 85 – 91;,
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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H3F3N2O

1,8-Diazabicyclo[5.4,0]undec-7-enium 5′-O-(tert-butyldiphenylsilyl)-3′-O-(tert-butyldimethylsilyl)uridin-3′-yl phosphonate (13u) (100 mumol) is dried by repeated coevaporations with dry pyridine and then dissolved in dry pyridine (1 mL). N,N’-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BopCl; 500 mumol) is added, and the mixture is stirred for 5 min. To the mixture, a solution of amino alcohol (L-2) (100 mumol), which has been dried by repeated coevaportions with dry pyridine and dissolved in dry pyridine (1 mL), is added dropwise via syringe, and the mixture is stirred for 5 min under argon. 2′,3′-O-bis(tert-butyldimethylsilyl)uridine 9u is dried by repeated coevaporations with dry pyridine and dissolved in 100 mumol pyridine. Then the above mixture is added via cannula into the solution of 2′,3′-O-bis(tert-butyldimethylsilyl)uridine 9u (100 |imol). After 10 min, N-trifluoroacctyl imidazole (CF3COIm; 200 mumol) is added. After an additional 30 s, N,N’-dimethylthiuram disulfide (DTD; 120 mumol) is added. After an additional 3 min, the mixture is dried in vacuum. To the residue, cone NH3-EtOH (3:1, v/v, 10 mL) is added, and the mixture is stirred for 12 h, and then concentrated to dryness under reduced pressure. Then, the mixture is diluted with CHCl3 (5 mL), and washed with 0.2 M phosphate buffer (pH 7.0, 5 mL). The aqueous layers are back-extracted with CHCl3 (2 *5 mL). The combined organic layers are dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue is purified by PTLC. The product is dissolved in CHCl3 (5 mL), washed with 0.2 M 1,8-diazabicyclo[5.4.0]undec-7-enium bicarbonate buffer (5 mL) and back-extracted with CHCl3 (2*5 mL). The combined organic layers are dried over Na2SO4, filtered, and concentrated to dryness to afford (Sp)-14uu.

According to the analysis of related databases, 1546-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONTORII INCORPORATED; VERDINE, GREGORY L; MEENA, MEENA; IWAMOTO, NAOKI; (250 pag.)JP2015/205910; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8,Some common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, molecular formula is C5H3F3N2O, 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.

5-(5-(4-Bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide (Step 4) To a stirred solution of hexamethyldisilazane (2.5 ml, 11.75 mmol) in tetrahydrofuran (25 ml) was added n-butyllithium (7.5 ml, 11.75 mmol) dropwise at 0 C. under nitrogen. The reaction mixture was stirred at room temperature for 30 min. Then cooled to -78 C., to the mixture was added a solution of 1-(4-bromo-3-fluorophenyl)-1-butanone (2.4 g, 9.79 mmol) in tetrahydrofuran (12 ml) dropwise and stirred at rt for 1 h. Then 1-trifluoroacetylimidazole (1.3 ml, 11.75 mmol) was added to the mixture at same temperature, the mixture was stirred at rt for 5 h. This was quenched by water and the pH was adjusted to pH 4-5, extracted with ethyl acetate. The extracts was dried (MgSO4) and concentrated. This was purified on silica gel eluding with ethyl acetate/hexane (1:20/1:15) to afford 2.7 g (80.9%) as a yellow oil. A mixture of 1-(4-bromo-3-fluorophenyl)-2-ethyl-4,4,4-trifluoro-1,3-butanedione (1.5 g, 4.40 mmol) and 5-hydrazino-2-pyridinesulfonamide hydrochloride (1.28 g, 5.72 mmol) in ethanol (60 ml) was stirred at reflux for 3 h. After cooling, the solvent was removed and the residue was diluted with ethyl acetate, washed with water. The extracts was dried (MgSO4), and concentrated. This was purified on silica gel eluding with ethyl acetate/hexane (1:10/1:5/1:4) to afford 1.64 g (75.6%) of the titled compound as a white amorphous. 1H-NMR (CDCl3) delta: 8.58-8.57 (1H, m), 7.99-7.95 (1H, m), 7.79 (1H, dd, J=8.6, 2.5 Hz), 7.70-7.64 (1H, m), 7.05 (1H, dd, J=8.6, 1.8 Hz), 6.91-6.88 (1H, m), 5.40 (2H, br.s), 2.56 (2H, q, J=7.6H), 1.14 (3H, t, J=7.6 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, its application will become more common.

Reference:
Patent; PFIZER INC.; US2003/144280; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

A small sample of the free base (50mg) was derivatized as its trifluoroacetyl analogue for chiral HPLC analysis. The sample was dissolved in acetonitrile (4ml) and treated with 1- (trifluoroacetyl)imidazole (0.4ml). The solution was stirred at 65 for 1 h, concentrated in vacuo and the residue dissolved in dichloromethane (5ml). The organic layer was washed with dilute sulphuric acid(2ml), then the organic layer concentrated and disssolved in hexane-isoproplyalcohol (98:2) for injection onto the HPLC column. Chiral HPLC (Chiracel-OD-H column, lot no. 09-02-20709, eluent hexane-isopropylalcohol 98:2, flow rate 1 ml/min, detection uv 230nm, temperature 40) retention time 12.93 mins.

The chemical industry reduces the impact on the environment during synthesis 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/90114; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of mutilin (93g, 0.29 mole) in EtOAc (1 L) was cooled to -45 0C (CH3CN/dry ice bath) with mechanical stirring under nitrogen. Trifluoroacetyl imidazole (Aldrich, 5 x 1Og ampules, 5Og, 0.30 mole) was then added dropwise over 30-45 minutes. After stirring for 1 hour, TLC (10% EtOAc/hexanes) showed complete consumption of mutilin. The mixture was allowed to ward to – 200C, and was then washed with IN HCl (2 x 30OmL), water, brine and then was dried over magnesium sulfate and filtered. After concentration to 300-40OmL, IL of hexanes was added with stirring. The precipitated product was filtered and washed with hexanes (IL) to afford pure 11-OTFA-mutilin as a white crytalline solid (55g). Additional product was obtained by evaporating the filtrate, and stirring the residue in ethyl ether (10OmL), and diluting with hexanes (40OmL). Filtration and washing with hexanes gave a second crop (47g) which was ~90% pure by NMR.

The synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/62334; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1546-79-8, 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 1546-79-8 as follows.

5-[4-Fluoro-5-(4-bromophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridinesulfonamide (Step 2) To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at -78 C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml*3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil.

According to the analysis of related databases, 1546-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; US2003/144280; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, A new synthetic method of this compound is introduced below.

General procedure: The compound 6b (35.1 mg, 50 mumol) was dried by repeated coevaporations with dry MeCN (3 mL) under Ar. The thymidine 3?-O-oxazaphospholidine derivative 7t (75.5 mg, 0.10 mmol), which was dried in vacuo overnight, and a 0.3 M solution of CMPT 8 (0.5 mL), which was dried over MS3A overnight, were successively added, and the mixture was stirred for 20 min at rt under Ar. N-(Trifluoroacetyl)imidazole (17.0 muL, 0.15 mmol) and i-Pr2NEt (44.0 muL, 0.25 mmol) were added and the mixture was stirred for 30 min at rt. Then DTD (31.9 mg, 0.15 mmol) was added and the mixture was stirred for 50 min at rt. The mixture was then concentrated under reduced pressure, and the residue was dissolved in dichloromethane (5.0 mL). A 6 vol% DCA solution in dichloromethane (5.0 mL) and Et3SiH (1.2 mL, 7.5 mmol) were added and the mixture was stirred for 20 min at rt. The mixture was washed with saturated NaHCO3 aqueous solutions (3 ¡Á 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 ¡Á 10 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by FSPE [1.6 cm column id, 4.8 g of fluorous silica gel, methanol-H2O 16 mL (80:20, v/v) then THF 25 mL] to give 14t, a, c or g as a colorless foam, which was analyzed by 31P NMR (Fig. 2). The 14t, a, c or g thus obtained was dissolved in ethanol (8.0 mL) and a 25% NH3 aqueous solution (40 mL) was added. The mixture was put in a sealed flask and heated at 55 C for 12 h while stirring. The mixture was then cooled to rt, concentrated under reduced pressure to ca. 20 mL The mixture was diluted with a 0.1 M ammonium acetate buffer (pH 7.0) (20 mL) and washed with CHCl3 (4 ¡Á 20 mL). The aqueous layer was then concentrated under reduced pressure. The residue was repeatedly lyophilized from distilled H2O to remove ammonium acetate to give crude the dinucleoside phosphorothioate (15t, a, c or g), which was analyzed by RP-HPLC [Senshu Pak PEGASIL ODS, 4 ¡Á 150 mm, linear gradient of 0-20% MeCN (60 min) in 0.1 M triethylammonium acetate buffer (pH 7.0), 50 C, 0.5 mL/min]. Authentic samples of 15t,a,c,g were synthesized via the solid-phase synthesis using the nucleoside 3?-O-oxazaphospholidines 7t,a,c,g as monomer units [8d].

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:
Article; Oka, Natsuhisa; Murakami, Ryosuke; Kondo, Tomoaki; Wada, Takeshi; Journal of Fluorine Chemistry; vol. 150; (2013); p. 85 – 91;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1546-79-8 name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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. 1546-79-8

A solution of 2-benzo [1, 3] dioxol-5-yl-l- (6-bromo-pyridin-2-yl)-ethanone (0. 359 mmol) in anhydrous THF (5 mL) was added to a slurry of sodium hydride (0. 725 mmol) in anhydrous THF (5 mL) at RT. After 5 minutes, N- TRIFLUOROACETYLIMIDAZOLE (0. 395 mmol) was added. After an additional 30 minutes at room temperature, hydrazine (1. 5 mL) was added. After another 30 minutes, glacial acetic acid (10 mL) was added and the reaction warmed to 100 C for 1 hour. The reaction was then concentrated in vacuo and purified via reverse phase HPLC (acetonitrile-water gradient) to give a solid identified as 2- (4-BENZO [1, 3] dioxol-5-yl-5- TRIFLUOROMETHYL-LH-PYRAZOL-3-YL)-6-BROMO-PYRIDINE : MS (ESP+) 411. 9 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2004/72033; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem