S News Extended knowledge of 1546-79-8

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.

Electric Literature 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

9/10/2021 News Analyzing the synthesis route of 1546-79-8

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 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., SDS of cas: 1546-79-8

Step 4 Preparation of 6-chloro-5,6-dihydro-3-trifluoroacetyl-4H-thieno[2,3-b]thiopyran-4-one The compound from Step 3 (1.03 g, 5.0 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to -78 C. A solution of sodium bistrimethylsilylamide (5.0 mL of a 1.0M tetrahydrofuran solution) was added and the reaction stirred for 0.75 hours at -78 C. Trifluoroacetyl imidazole (0.68 mL, 6.0 mmol) was added and the reaction was warmed to room temperature and stirred under a nitrogen atmosphere for 16 hours. At this time, 1N hydrochloric acid (300 mL) was added to the reaction followed by extraction with ether (350 mL). The organics were washed with brine (200 mL), dried over MgSO4 and concentrated in vacuo. The resulting yellow oil was used without further purification.

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 1546-79-8.

Reference:
Patent; Talley; John J.; Bertenshaw; Stephen R.; Graneto; Matthew J.; Rogier; Donald J.; US5547975; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some tips on C5H3F3N2O

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, 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, 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 1546-79-8, SDS of cas: 1546-79-8

The thymidine 3?-O-oxazaphospholidine derivative 7t (75.5 mg, 0.10 mmol) was dried by coevaporation with dry MeCN (3 mL) under Ar and dissolved in a 0.3 M solution of CMPT 8 (0.5 mL), which was dried over MS3A overnight. The resultant solution was added to the compound 6a (40.1 mg, 50 mumol), which was dried by coevaporation with dry MeCN prior to use, and the resultant 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 × 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 × 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 13t (73.3 mg, colorless foam), which was analyzed by 31P NMR (121 MHz, CDCl3) delta 68.9.

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, 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

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

New learning discoveries about 1546-79-8

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.

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., Quality Control of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone

1,8-diazabicyclo[5.4.0]undec-7-enium 5′-O-(tert-butyldiphenylsilyl)-2′-O-(tert-butyldimethylsilyl)uridine-3′-yl phosphonate (8u) (100 mumol) are dried by repeated co-evaporation with anhydrous pyridine and then dissolved in anhydrous pyridine (1 mL). N,N’-bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (BopCl; 500 mumol) is added and the mixture is allowed to stir for 5 minutes.To the mixture, a solution of amino alcohol (L-2) (100 mumol) dissolved in anhydrous pyridine (1 mL) was added dropwise by syringe and the mixture was stirred for 5 min under argon. 2′,3′-O-bis((tert-butyldimethylsilyl)uridine 9u is dried using repeated co-evaporation with anhydrous pyridine and dissolved in 100 mumol pyridine. Thereafter, the mixture is added via cannula to a solution of 2′,3′-O-bis(tert-butyldimethylsilyl)uridine 9u (100 mumol). After 10 minutes N-trifluoroacetylimidazole (CF3COIm; 200 mumol) is added. After an additional 30 seconds N,N’-dimethylthiuram disulfide (DTD; 120 mul) is added. After a further 3 minutes the mixture is dried in vacuo. Concentrated NH3-EtOH (3: 1, v / v, 10 mL) is added to the residue and the mixture is allowed to stir for 12 hours, then concentrated to dryness under reduced pressure. Thereafter, the mixture is diluted with CHCl3 (5 mL) and washed with 0.2 M phosphate buffer (pH 7.0, 5 mL). The aqueous layer is back-extracted with CHCl3 (2 × 5 mL). The organic layers are combined, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue is purified by preparative TLC. The product was dissolved in CHCl3 (5 mL), washed with 0.2 M 1,8-diazabicyclo [5.4.0] undec-7-enium bicarbonate buffer (5 mL) and washed with CHCl3 (2 × 5 mL) Back extracted. Combine the organic layers, dry over Na2SO4, filter, concentrate and dry to give (SP)-10uu.

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

Extended knowledge of 1546-79-8

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 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., Product Details of 1546-79-8

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 × 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 × 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 × 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 × 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].

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 1546-79-8.

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

Research on new synthetic routes about 1546-79-8

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 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.

To a solution of 1,3-cyclohexanedione (561 mg, 5.0 mmol) and imidazole (340 mg, 5.0 mmol) in CH2C12 (50 ml) was added neat N-trifluoroacetyl imidazole (2.27 ml, 20 mmol). The reaction mixture was stirred at room temperature for 45min. The reaction was diluted with 4N aq. HCl and the layers were separated. The aqueous layer was extracted 2x CH2C12. The combined organics were washed with H20 and brine. The organics were dried over MgS04, filtered and concentrated. The crude product was used directly for the next step.

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; GILEAD SCIENCES, INC.; BONDY, Steven S.; CANNIZZARO, Carina E.; CHOU, Chien-hung; HALCOMB, Randall L.; HU, Yunfeng Eric; LINK, John O.; LIU, Qi; SCHROEDER, Scott D.; TSE, Winston C.; ZHANG, Jennifer R.; WO2013/6738; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1546-79-8

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.

Electric Literature 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.

Example 22b (racemic mixture)Ethylmagnesium bromide (3M in ethyl ether, 3.95 ml, 11.84 mmol) is added dropwise to example 21a (1.6 g, 5.92 mmol) dissolved in anhydrous THF (20 mL) cooled to 0C. Stirring is continued at 0C for 15 min then overnight at room temperature. The reaction mixture is cooled to 0C and methylmagnesium bromide (3M in ethyl ether, 1.97 ml, 5.92 mmol) is added dropwise. Stirring is continued at 0C for 15 min followed by 2h at room temperature. The reaction mixture is cooled to 0C, aqueous NH4C1 is added dropwise and stirring is continued for 5 min. EtOAc is added, the organic layer separated, washed with brine, dried over Na2SC”4 and concentrated under reduced pressure to furnish 1.37 g of crude ketone. Lithium bis(trimethylsilyl)amide (1,8M, 1.03 mL, 1.86 mmol) is added dropwise to the crude ketone (370 mg, 1.55 mmol) dissolved in anhydrous THF (10 mL) and cooled to -78C. Stirring is continued at -20C for lh. The reaction mixture is cooled to -78C and l-(trifluoroacetyl)imidazole (0.70 ml, 6.18 mmol) is added. Stirring is continued 3 h at room temperature. Aqueous NH4C1 solution and EtOAc are added, the organic layer is separated, dried over a phase-separator cartridge and concentrated under reduced pressure to furnish a residue that is purified by Si flash chromatography (5-40% EtOAc/Hexane as eluent) to obatain 190 mg of intermediate. Hydro xylamine hydrochloride (512 mg, 7.37 mmol) is added to such product dissolved in MeOH (20 mL) and the reaction mixture refluxed for 2h. Volatiles are evaporated under reduced pressure, the residue is partitioned between EtOAc and saturated NaHCC>3, the organic layer is separated, washed with saturated NaHCC>3, dried over phase separator cartridge and concentrated under reduced pressure to furnish a 90mg of residue. TEA (50 mu, 0.36 mmol) followed by methanesulfonyl chloride (26 mu, 0.33 mmol) are added to such residue dissolved in DCM (10 mL) and cooled to 0C. Stirring is continued at room temperature then further TEA (50 mu, 0.36 mmol) and methanesulfonyl chloride (26 mu,, 0.33 mmol) are added and stirring is continued for 2h. Water and DCM are added, the aqueous layer is further extracted with DCM, the organic layers are combined, dried over a phase-separator cartridge and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (eluent 0-10% EtOAc/hexane) to furnish the title compound (20 mg, 23% on the last step).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; WO2013/17657; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Analyzing the synthesis route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone

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 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., Quality Control of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone

Step 4 Preparation of 6-chloro-5,6-dihydro-3-trifluoroacetyl-4H-thieno[2,3-b]thiopyran-4-one The compound from Step 3 (1.03 g, 5.0 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to -78 C. A solution of sodium bistrimethylsilylamide (5.0 mL of a 1.0M tetrahydrofuran solution) was added and the reaction stirred for 0.75 hours at -78 C. Trifluoroacetyl imidazole (0.68 mL, 6.0 mmol) was added and the reaction was warmed to room temperature and stirred under a nitrogen atmosphere for 16 hours. At this time, 1N hydrochloric acid (300 mL) was added to the reaction followed by extraction with ether (350 mL). The organics were washed with brine (200 mL), dried over MgSO4 and concentrated in vacuo. The resulting yellow oil was used without further purification.

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 1546-79-8.

New downstream synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1546-79-8, its application will become more common.

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. Recommanded Product: 1546-79-8

To a solution of 5 (1.54 g, 2.67 mmol) in THF (40 mL) was added 1-(trifluoroacetyl)imidazole (365 mL, 3.20 mmol), and the whole was heated for6 h under reflux. After being cooled to room temperature, the reactionmixture was quenched by addition of ice, and the solvent was removedin vacuo. The residue was partitioned between AcOEt and H2O. The separatedorganic layer was further washed with H2O (twice) and saturatedaqueous NaHCO3, followed by brine. The separated organic layer wasdried and concentrated in vacuo. The residue was purified by a silica gelcolumn, eluted with MeOH in CHCl3 (0%-4%), to give 6 (1.30 g, 84% asa white solid): ESI-LRMS m/z 601 (MNa); ESI-HRMS calcd forC29H54N4O4NaSi2 601.3581, found 601.3539; 1H NMR (400 MHz, CDCl3)d 7.73 (1 H, s, H-2), 7.01 (1 H, br s, NH2, exchangeable with D2O), 6.09(1 H, dd, H-1?, J5.4, 8.3 Hz), 5.39 (1 H, br s, NH2, exchangeable withD2O), 4.88 (1 H, d, CH2, J18.0 Hz), 4.72 (1 H, dd, H-3?, J2.3, 5.3 Hz),4.13-4.08 (2 H, m, H-4?,CH2), 3.90-3.83 (2 H, m, H-5?), 2.55 (1 H, ddd,H-2?a, J5.4, 13.0, 2.3 Hz), 2.44 (1 H, ddd, H-2?b, J8.3, 13.0, 5.3 Hz),1.16-1.02 (42 H, m, TIPS); 13C NMR (100 MHz, CDCl3) d 165.08, 134.74,132.94, 124.22, 115.69, 89.14, 85.36, 72.78, 63.57, 42.63, 18.09, 18.06,13.14, 12.18, 11.99.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1546-79-8, its application will become more common.

Brief introduction of 1546-79-8

The synthetic route of 1546-79-8 has been constantly updated, and we look forward to future research findings.

Reference of 1546-79-8, 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.

Ethylmagnesium bromide (3M in ethyl ether, 3.95 ml, 11.84 mmol) is added dropwise to example 21a (1.6 g, 5.92 mmol) dissolved in anhydrous THF (20 mL) cooled to 0 C. Stirring is continued at 0 C. for 15 min then overnight at room temperature. The reaction mixture is cooled to 0 C. and methylmagnesium bromide (3M in ethyl ether, 1.97 ml, 5.92 mmol) is added dropwise. Stirring is continued at 0 C. for 15 min followed by 2 h at room temperature. The reaction mixture is cooled to 0 C., aqueous NH4Cl is added dropwise and stirring is continued for 5 min EtOAc is added, the organic layer separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to furnish 1.37 g of crude ketone. Lithium bis(trimethylsilyl)amide (1.8M, 1.03 mL, 1.86 mmol) is added dropwise to the crude ketone (370 mg, 1.55 mmol) dissolved in anhydrous THF (10 mL) and cooled to -78 C. Stirring is continued at -20 C. for 1 h. The reaction mixture is cooled to -78 C. and 1-(trifluoroacetyl)imidazole (0.70 ml, 6.18 mmol) is added. Stirring is continued 3 h at room temperature. Aqueous NH4Cl solution and EtOAc are added, the organic layer is separated, dried over a phase-separator cartridge and concentrated under reduced pressure to furnish a residue that is purified by Si flash chromatography (5-40% EtOAc/Hexane as eluent) to obatain 190 mg of intermediate. Hydroxylamine hydrochloride (512 mg, 7.37 mmol) is added to such product dissolved in MeOH (20 mL) and the reaction mixture refluxed for 2 h. Volatiles are evaporated under reduced pressure, the residue is partitioned between EtOAc and saturated NaHCO3, the organic layer is separated, washed with saturated NaHCO3, dried over phase separator cartridge and concentrated under reduced pressure to furnish a 90 mg of residue. TEA (50 muL, 0.36 mmol) followed by methanesulfonyl chloride (26 muL, 0.33 mmol) are added to such residue dissolved in DCM (10 mL) and cooled to 0 C. Stirring is continued at room temperature then further TEA (50 muL, 0.36 mmol) and methanesulfonyl chloride (26 muL, 0.33 mmol) are added and stiffing is continued for 2 h. Water and DCM are added, the aqueous layer is further extracted with DCM, the organic layers are combined, dried over a phase-separator cartridge and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (eluent 0-10% EtOAc/hexane) to furnish the title compound (20 mg, 23% on the last step).

The synthetic route of 1546-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; US2013/197011; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem