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[ CAS No. 1546-79-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1546-79-8
Chemical Structure| 1546-79-8
Chemical Structure| 1546-79-8
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Product Details of [ 1546-79-8 ]

CAS No. :1546-79-8 MDL No. :MFCD00014501
Formula : C5H3F3N2O Boiling Point : -
Linear Structure Formula :- InChI Key :SINBGNJPYWNUQI-UHFFFAOYSA-N
M.W : 164.09 Pubchem ID :73767
Synonyms :

Calculated chemistry of [ 1546-79-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 28.91
TPSA : 34.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 0.78
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : -0.07
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : 1.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.55
Solubility : 4.59 mg/ml ; 0.028 mol/l
Class : Very soluble
Log S (Ali) : -1.09
Solubility : 13.2 mg/ml ; 0.0807 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.24
Solubility : 9.53 mg/ml ; 0.0581 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 1546-79-8 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1546-79-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1546-79-8 ]

[ 1546-79-8 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 188290-36-0 ]
  • [ 1546-79-8 ]
  • [ 651-70-7 ]
  • 2
  • [ 534-22-5 ]
  • [ 1546-79-8 ]
  • [ 18087-60-0 ]
  • 3
  • [ 51549-31-6 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid (2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2,2,2-trifluoro-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • 4
  • [ 51549-30-5 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(2,2,2-trifluoro-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester [ No CAS ]
  • 5
  • [ 54925-54-1 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid (2R,3S,5R)-3-(1-isopropyl-silolan-1-yloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • 6
  • [ 54925-53-0 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid (2R,3S,5R)-2-(1-isopropyl-silolan-1-yloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
  • 7
  • [ 54925-60-9 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid (2R,3S,5R)-3-(1-tert-butyl-silolan-1-yloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • 8
  • [ 54925-59-6 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid (2R,3S,5R)-2-(1-tert-butyl-silolan-1-yloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
  • 9
  • [ 130451-27-3 ]
  • [ 18156-74-6 ]
  • [ 120240-10-0 ]
  • [ 1546-79-8 ]
  • 10
  • [ 13523-86-9 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid 1-[isopropyl-(2,2,2-trifluoro-acetyl)-amino]-methyl}-2-[1-(2,2,2-trifluoro-acetyl)-1H-indol-4-yloxy]-ethyl ester [ No CAS ]
  • 11
  • [ 71953-76-9 ]
  • [ 1546-79-8 ]
  • (6aR,9S)-4-(2,2,2-Trifluoro-acetyl)-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid diethylamide [ No CAS ]
  • 12
  • [ 1546-79-8 ]
  • [ 40733-27-5 ]
  • Trifluoro-acetic acid (2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • 13
  • [ 1546-79-8 ]
  • [ 40733-28-6 ]
  • Trifluoro-acetic acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
  • 14
  • [ 1546-79-8 ]
  • [ 38554-86-8 ]
  • (6aR,9S)-7-Methyl-4-(2,2,2-trifluoro-acetyl)-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl-propyl-amide [ No CAS ]
  • 15
  • [ 1546-79-8 ]
  • [ 525-66-6 ]
  • [ 40435-87-8 ]
  • 16
  • [ 1546-79-8 ]
  • [ 2126-78-5 ]
  • (6aR,9S)-7-Methyl-4-(2,2,2-trifluoro-acetyl)-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid diethylamide [ No CAS ]
  • 17
  • [ 1546-79-8 ]
  • [ 50-37-3 ]
  • N-trifluoroacetyllysergic acid diethylamide [ No CAS ]
  • 18
  • [ 4292-19-7 ]
  • [ 1546-79-8 ]
  • [ 26944-42-3 ]
  • 19
  • [ 1776-08-5 ]
  • [ 1546-79-8 ]
  • [ 160856-31-5 ]
  • 20
  • [ 2033-24-1 ]
  • [ 1546-79-8 ]
  • [ 693817-83-3 ]
  • 21
  • [ 6285-05-8 ]
  • [ 1546-79-8 ]
  • 1-(4-Chloro-phenyl)-4,4,4-trifluoro-2-methyl-butane-1,3-dione [ No CAS ]
  • 22
  • [ 450-95-3 ]
  • [ 1546-79-8 ]
  • [ 188817-19-8 ]
  • 23
  • [ 4981-63-9 ]
  • [ 1546-79-8 ]
  • 1-(4-Chloro-phenyl)-2-ethyl-4,4,4-trifluoro-butane-1,3-dione [ No CAS ]
  • 24
  • [ 709-24-0 ]
  • [ 1546-79-8 ]
  • 4,4,4-Trifluoro-1-(4-fluoro-phenyl)-2-propyl-butane-1,3-dione [ No CAS ]
  • 25
  • [ 87483-29-2 ]
  • [ 1546-79-8 ]
  • [ 165252-27-7 ]
  • 26
  • [ 1546-79-8 ]
  • [ 244024-09-7 ]
  • C22H37F3O4Si [ No CAS ]
  • 27
  • [ 61-54-1 ]
  • [ 1546-79-8 ]
  • [ 90704-74-8 ]
  • 28
  • [ 61-49-4 ]
  • [ 1546-79-8 ]
  • ω-N-Bis-trifluoracetyl-N-methyltryptamin [ No CAS ]
  • 29
  • [ 61-50-7 ]
  • [ 1546-79-8 ]
  • 1-[3-(2-dimethylamino-ethyl)-indol-1-yl]-2,2,2-trifluoro-ethanone [ No CAS ]
  • 30
  • [ 608-07-1 ]
  • [ 1546-79-8 ]
  • 2,2,2-trifluoro-<i>N</i>-[2-(5-methoxy-1-trifluoroacetyl-1<i>H</i>-indol-3-yl)-ethyl]-acetamide [ No CAS ]
  • 31
  • [ 487-93-4 ]
  • [ 1546-79-8 ]
  • Trifluoro-acetic acid 3-(2-dimethylamino-ethyl)-1-(2,2,2-trifluoro-acetyl)-1H-indol-5-yl ester [ No CAS ]
  • 32
  • [ 1019-45-0 ]
  • [ 1546-79-8 ]
  • 1-[3-(2-dimethylamino-ethyl)-5-methoxy-indol-1-yl]-2,2,2-trifluoro-ethanone [ No CAS ]
  • 33
  • [ 1546-79-8 ]
  • [ 7518-21-0 ]
  • [ 111217-41-5 ]
  • 36
  • [ 1125-99-1 ]
  • [ 1546-79-8 ]
  • [ 187726-38-1 ]
  • 37
  • [ 1546-79-8 ]
  • [ 83329-71-9 ]
  • 38
  • [ 99-90-1 ]
  • [ 1546-79-8 ]
  • [ 18931-61-8 ]
  • 39
  • [ 1546-79-8 ]
  • C13H18F3N5O6 [ No CAS ]
  • 40
  • [ 603972-35-6 ]
  • [ 1546-79-8 ]
  • [ 603972-36-7 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran; toluene; at 0℃; for 0.166667h; After coevaporation with toluene, 4 (393 mg; 0.75 mmole) was combined with trifluoroacetylimidazole (94 uL; 0.83 mmole) in 5 ml dry THF at 0 C., and stirred for 10 minutes. The solvent was evaporated, and the oily residue taken up in 50 ml EtOAc, extracted 2× with saturated aqueous NaHCO3, 1× with saturated aqueous NaCl, dried with NaSO4, and evaporated to yield 475 mg (99%) of the N-TFA protected nucleoside 5 as a colorless oil
  • 41
  • aminobutyl nucleoside [ No CAS ]
  • [ 1546-79-8 ]
  • TFA-protected nucleoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In acetonitrile; at 0℃; for 2h; This was converted directly to the TFA-protected nucleoside (22) by reaction with 1-trifluoroacetylimidazole (300 uL; 1.8 mmole) in 3 ml ACN at 0 C. for 2 hours, evaporating the solvent and purifying by flash chromatography (1:9 MeOH-DCM). Yield 175 mg (0.42 mmole; 93%). Identity of the product was confirmed by 1H-nmr and mass spectrometry.
  • 42
  • C11H16N4O6 [ No CAS ]
  • [ 1546-79-8 ]
  • C13H15F3N4O7 [ No CAS ]
  • 43
  • acrylate [ No CAS ]
  • [ 1546-79-8 ]
  • acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% The acrylate 40 was then treated with neat ethylenediamine (2 ml, excess) and two drops of TEA and heated to 100 C. After 1 hour the excess EDA was evaporated, yielding 146 mg of the free amine (quantitative). The crude residue was then co-evaporated with pyridine (3×, 5 ml, insoluble), resuspended in a mixture of pyridine and DMF and was cooled to 0 C. To this mixture was added TFA-imidazole (73.8 mg, 1.1 eq.). The reaction was then allowed to warm to room temperature and stirred overnight. An additional 1 eq. of TFA-imidazole was added at this time and the reaction was stirred an additional 15 minutes. The solvent was then evaporated, and the residue was co-evaporated with water(2×, 5 ml) and dissolved in 5 ml of water. The white precipitate that formed was removed by filtration. The mother liquor, which contained the TFA-protected nucleoside 3, was separated into two aliquots and purified by reverse phase HPLC. The fractions were then pooled and evaporated to yield 20% (35 mg) of pure 41, which was verified by 'H NMR
  • 44
  • 1-[4-bromo-3-(trifluoromethyl)phenyl]-1-ethanone [ No CAS ]
  • [ 1546-79-8 ]
  • [ 252562-64-4 ]
YieldReaction ConditionsOperation in experiment
1.80 g (88%) With hydrogenchloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1-[4-Bromo-3-(trifluoromethyl)phenyl]-4,4,4-trifluoro-1,3-butanedione (step 4) To a solution of 1-[4-bromo-3-(trifluoromethyl)phenyl]-1-ethanone (1.34 g, 5.65 mmol) in THF (30 ml) was added lithium bis(trimethylsilyl)amide (1.0 M THF solution, 6.8 ml, 6.8 mmol) at -78 C. The mixture was stirred at 0 C. for 15 minutes and the solution was again cooled to -78 C. <strong>[1546-79-8]N-trifluoroacetylimidazole</strong> (1.15 g, 6.78 mmol) was added to the solution at the same temperature. The resulting mixture was stirred at -78 C. for 15 minutes and at room temperature for 2.5 hours. The reaction was quenched with 2N HCl (100 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 ml*2). The combined organic layer was washed with brine (200 ml), dried over MgSO4, and concentrated in vacuo to give 1.80 g (88%) of the title compound as a pale yellow solid. 1H-NMR (CDCl3) delta: 8.23 (1H, d, J=2.1 Hz), 7.93 (1H, dd, J=1.8, 8.4 Hz), 7.89 (1H, d, J=8.4 Hz), 6.57 (1H, s).
  • 45
  • [ 4981-64-0 ]
  • [ 1546-79-8 ]
  • [ 343564-19-2 ]
YieldReaction ConditionsOperation in experiment
5.64 g (69%) With hydrogenchloride; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 1-(4-Bromophenyl)-2-ethyl-4,4,4-trifluoro-1,3-butanedione (Step 3) To a solution of hexamethyldisilazane (4.92 g, 30.5 mmol) in THF (10 ml) was added dropwise n-BuLi (1.57 M hexane solution, 19.4 ml, 30.5 mmol) at -78 C. and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled down to -78 C. again and 1-(4-bromophenyl)-1-butanone (5.77 g, 25.4 mmol) in THF (25 ml) was added dropwise over 15 min. The resulting mixture was stirred at -78 C. for 30 minutes, then allowed to warm up to 0 C. and stirred for 40 minutes. The solution was recooled down to -78 C. and <strong>[1546-79-8]N-trifluoroacetylimidazole</strong> (5.00 g, 30.5 mmol) was added. The mixture was stirred at -78 C. for 20 minutes, and at room temperature for 2 hours. The reaction was quenched with 2N HCl (30 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml*2). The combined organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1) to give 5.64 g (69%) of the title compound as a oil. TLC: Rf=0.35 (hexane/ethyl acetate=5/1).
  • 46
  • [ 343564-57-8 ]
  • [ 343564-59-0 ]
  • [ 343262-53-3 ]
  • [ 1546-79-8 ]
  • [ 343564-58-9 ]
YieldReaction ConditionsOperation in experiment
1.64 g (75.6%) With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; ethanol; 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)
  • 47
  • [ 403-30-5 ]
  • [ 1546-79-8 ]
  • [LiN(SiMe3)2]2(THF)2 [ No CAS ]
  • [ 343564-26-1 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; 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., <strong>[1546-79-8]N-trifluoroacetylimidazole</strong> (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.
  • 48
  • [ 1546-79-8 ]
  • [ 343564-44-3 ]
  • [ 343564-46-5 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 4-(1-(6-aminosulfonyl-3-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl)-2-fluorophenyl trifluoromethanesulfonate (Step 3) To a stirred solution of hexamethyldisilazane (6.4 ml, 30.36 mmol) in tetrahydrofuran (65 ml) was added n-butyllithium (19.3 ml, 30.36 mmol) dropwise at 0 C. under nitrogen. The reaction mixture was stirred at 0 C. for 30 min. Then cooled to -78 C., to the mixture was added a solution of 4-acetyl-2-fluorophenyltrifluoromethanesulfonate (7.24 g, 25.30 mmol) in tetrahydrofuran (30 ml) dropwise and stirred at -78 C. for 1 h. Then 1-trifluoroacetylimidazole (3.5 ml, 30.36 mmol) was added to the mixture at same temperature and the mixture was stirred at -78 C. for 3 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 (1:10/1:8/1:4) to afford 2-fluoro-4-(4,4,4-trifluoro-3-oxobutanoyl)phenyltrifluoromethanesulfonate (3.0 g) as a red oil.
  • 49
  • (4-tert-butyldimethylsilyloxy)-3-chlorophenyl-1-ethanone [ No CAS ]
  • [ 1546-79-8 ]
  • [ 343564-34-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; water; 1-(4-tert-Butyldimethylsilyloxy)-3-chlorophenyl-4,4,4-trifluoro-1,3-butanedione (Step 2) To a solution of hexamethyldisilazane (1.8 mL, 8.4 mmol) in THF (20 mL), n-BuLi (1.53 M in n-hexane, 5.5 mL, 8.4 mmol) was added at 0 C. and stirred for 30 min at 0 C. The mixture was cooled to -70 C. and [(4-tert-butyldimethylsilyloxy)-3-chlorophenyl-1-ethanone (from step 1, 2.0 g, 7.0 mmol) in THF (10 mL) was added dropwise and the mixture was stirred for 1 h at -70 C. Then trifluoroacetylimidazole (0.96 mL, 8.4 mmol) was added at -70 C. and the mixture was stirred for further 2 hours and water (30 mL) was added. 2N aqueous HCl was added to adjust pH to 4and extracted with ethyl acetate (100 mL*2), dried over MgSO4, and concentrated in vacuo gave pale red brown oil. (2.5 g, 93%) 1H-NMR (CDCl3) delta: 7.99 (s, 1H), 7.76 (d, J=8.0 Hz, 1H), 6.48 (d, J=8.0 Hz, 1H), 6.48 (s, 1H), 1.04 (s, 9H), 0.28 (s, 6H).
  • 50
  • [ 16994-31-3 ]
  • [ 1070-89-9 ]
  • [ 1546-79-8 ]
  • [ 178974-86-2 ]
YieldReaction ConditionsOperation in experiment
48% With hydrogenchloride; In tetrahydrofuran; Step 4. Preparation of 7-methoxy-3-(trifluoroacetyl)-isothiochroman-4-one. 7-Methoxyisothiochroman-4-one from Step 3 (0.58 g, 3.0 mmol) was dissolved in tetrahydrofuran (30 mL) and cooled to -78 C. A solution of sodium bistrimethylsilylamide (3.0 mL of a 1.0M tetrahydrofuran solution) was added and the reaction stirred for 0.5 hours at -78 C. Trifluoroacetyl imidazole (0.41 mL, 3.6 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 (200 mL) was added to the reaction followed by extraction with ether (250 mL). The organics were washed with brine (150 mL), dried over MgSO4 and concentrated in vacuo. The resulting yellow oil (0.42 g, 48%) was used without further purification.
  • 51
  • 6-chloro-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one [ No CAS ]
  • [ 1070-89-9 ]
  • [ 1546-79-8 ]
  • 6-chloro-5,6-dihydro-3-trifluoroacetyl-4H-thieno[2,3-b]thiopyran-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; 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.
  • 52
  • 3-[2-(1-hydroxy-3-hydroxyiminopropyl)benzothiazol-6-yl]-5-methoxymethyl-2-oxazolidinone [ No CAS ]
  • [ 1546-79-8 ]
  • (5R)-3-[2-((1S)-3-Cyano-1-hydroxypropyl)benzothiazol-6-yl]-5-methoxymethyl-2-oxazolidinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; Example 9 3-[2-(1(S)-Hydroxy-3-cyanopropyl)benzothiazol-6-yl]-5(R)-methoxymethyl-2-oxazolidinone STR47 73 g of the 3-[2-(1-hydroxy-3-hydroxyiminopropyl)benzothiazol-6-yl]-5-methoxymethyl-2 -oxazolidinone obtained in the Example 8 was dissolved in 800 ml of tetrahydrofuran. 90 g of trifluoroacetylimidazole was added dropwise to the solution under cooling with ice and the mixture was stirred at room temperature for 4 h. The reaction liquid was poured into an aqueous sodium hydrogencarbonate solution. After extraction with ethyl acetate followed by washing with an aqueous common salt solution, drying over magnesium sulfate and concentration under reduced pressure, the obtained solid was recrystallized from acetone/water to give 51 g of the titled compound. 1 H-NMR (CDCl3)delta: 2.1~2.4 (2H, m), 2.5~2.7 (2H, m), 3.42 (3H, s), 3.6~3.7 (2H, m) (3.9~4.1 (2H, m), 3.60 (1H, d), 4.7~4.9 (1H, m), 5.1~5.2 (1H, m), 7.50 (1H, dd), 7.83 (1H, d), 8.15 (1H, d)
  • 53
  • [ 93-55-0 ]
  • [ 1546-79-8 ]
  • [ 322-06-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hexamethyldisilazane; In tetrahydrofuran; Step 1 Preparation of 2-methyl-1-phenyl-4,4,4-trifluorobutane-1,3-dione To a solution of propiophenone (965 mg, 7.2 mmol) in THF (20 mL) at -78 C. was added sodium bis(trimethylsilyl)amide (7.9 mL of a 1M solution in THF). The solution was kept at -78 C. for 0.5 hour and then warmed to -20 C. over 1 hour. The solution was cooled to -78 C. and 1-(trifluoroacetyl)imidazole (1.5 g, 9.1 mmol) in THF (4 mL) was added via cannula. The solution was warmed to room temperature and stirred overnight. The mixture was partitioned between 1N HCl and ether. The organic solution was dried (Na2 SO4) and concentrated to give the crude diketone (1.9 g).
With sodium hexamethyldisilazane; In tetrahydrofuran; Step 1: Preparation of 2-methyl-1-phenyl-4,4,4-trifluorobutane-1,3-dione To a solution of propiophenone (965 mg, 7.2 mmol) in THF (20 mL) at -78 C. was added sodium bis(trimethylsilyl)amide (7.9 mL of a 1M solution in THF). The solution was kept at -78 C. for 0.5 hour and then warmed to -20 C. over 1 hour. The solution was cooled to -78 C. and 1-(trifluoroacetyl)imidazole (1.5 g, 9.1 mmol) in THF (4 mL) was added via cannula. The solution was warmed to room temperature and stirred overnight. The mixture was partitioned between 1N HCl and ether. The organic solution was dried (Na2 SO4) and concentrated to give the crude diketone (1.9 g).
  • 54
  • [ 6040-37-5 ]
  • [ 1546-79-8 ]
  • [ 193537-72-3 ]
YieldReaction ConditionsOperation in experiment
85% In ethyl acetate; at -45℃; for 1.5 - 1.75h;Cooling with acetonitrile-dry ice; 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.
  • 55
  • [ 288-32-4 ]
  • [ 407-25-0 ]
  • [ 1546-79-8 ]
YieldReaction ConditionsOperation in experiment
79% In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; This compound was prepared by modified procedure publishedearlier.14 To a pre-cooled (5 C) and well-stirred absolute THF(100 mL) trifluoroacetic anhydride (80 g, 380 mmol) was addedcarefully. The solution formed was added to a pre-cooled (5 C) andwell-stirred solution of imidazole (51.6 g, 759 mmol) in absoluteTHF (240 mL) carefully. The mixture was stirred for 1 h at ambienttemperature, and left at 0 C overnight. The solid precipitate wasfiltered off and washed with diethyl ether (25 mL). The filtrate wasconcentrated in vacuo without heating and the residuewas distilledto provide the desired product. Yield 49 g (79%), hydrolyticallysensitive colorless liquid, very moisture sensitive, bp 73e75 C(100 Torr) (lit.14 45e46 C (14 Torr)). 1H NMR (CDCl3) d: 7.21 (dd, 1H,H-4, J 1.8, 0.8 Hz), 7.55 (m, 1H, H-5), 8.24 (s, 1H, H-2). 19F NMR(CDCl3) d: 71.3 (s, CF3). The parameters in agreement with published data.15
  • 56
  • [ 4341-24-6 ]
  • [ 1546-79-8 ]
  • [ 950908-40-4 ]
  • 57
  • [ 493-72-1 ]
  • [ 1546-79-8 ]
  • [ 950908-42-6 ]
  • 58
  • [ 1774-12-5 ]
  • [ 1546-79-8 ]
  • [ 950908-43-7 ]
  • 59
  • [ 59373-32-9 ]
  • [ 1546-79-8 ]
  • [ 950908-41-5 ]
  • 60
  • [ 504-02-9 ]
  • [ 1546-79-8 ]
  • [ 950908-39-1 ]
YieldReaction ConditionsOperation in experiment
With 1H-imidazole; In dichloromethane; at 20℃; for 0.75h; 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.
  • 61
  • [ 126-81-8 ]
  • [ 1546-79-8 ]
  • [ 893842-26-7 ]
  • 62
  • [ 530-62-1 ]
  • [ 76-05-1 ]
  • [ 1546-79-8 ]
  • 63
  • [ 1546-79-8 ]
  • [ 136871-75-5 ]
  • [2S]-phenyl-piperidin-[3S]-ylamine 1-(trifluoroacetyl)imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 65℃; for 1h; 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.
  • 64
  • [ 1546-79-8 ]
  • [ 121-97-1 ]
  • [ 1076195-14-6 ]
YieldReaction ConditionsOperation in experiment
Method H[0370] A solution of the ketone (1 eq) in THF (20 vol) was added dropwise to a separate solution of LHMDS (1.2 eq) in THF (30 vol) at -78 0C and stirred for 1 h at this temperature. l-(Trifluoroacetyl)imidazole (4 eq) was then added dropwise and the reaction stirred for 1 h at -78 0C then 5 h at rt. The reaction mixture was poured onto ice (50 vol) and acidified to pH 1 with 1.2 M HCl. The aqueous solution was extracted with EtOAc (3 x 60 vol) and the combined organic layers washed with cold brine (1 x 60 vol), dried (Na2SO4), filtered and evaporated. The crude residue was purified by column chromatography (silica gel, 5% EtOAc in heptanes).; Example 7. 4,4,4-Trifluoro-l-(4-methoxyphenyl)-2-methyl-l,3-butanedione (7); [0377] 4'-Methoxypropiophenone (500 mg, 3.04 mmol) was treated with LHMDS (6.09 mL, 6.09 mmol, 1 M solution in THF) and l-(trifluoroacetyl)imidazole (1.38 mL, 12.1 mmol, d 1.441) using Method H to give the title compound as a pale yellow oil: 1H NMR deltaH (250 MHz, CDCl3) 7.97 (2H, d), 7.02 (2H, d), 4.90 (IH, q), 3.93 (3H, s), 1.56 (3H, d).
  • 65
  • CHF3O3S*C118H155F6N11O31P3PolS3Si4 [ No CAS ]
  • [ 1546-79-8 ]
  • C120H154F9N11O32P3PolS3Si4 [ No CAS ]
  • 66
  • CHF3O3S*C118H155F6N11O31P3PolS3Si4 [ No CAS ]
  • [ 1546-79-8 ]
  • C120H154F9N11O32P3PolS3Si4 [ No CAS ]
  • 67
  • CHF3O3S*C146H192F9N14O39P4PolS4Si5 [ No CAS ]
  • [ 1546-79-8 ]
  • C148H191F12N14O40P4PolS4Si5 [ No CAS ]
  • 68
  • CHF3O3S*C146H192F9N14O39P4PolS4Si5 [ No CAS ]
  • [ 1546-79-8 ]
  • C148H191F12N14O40P4PolS4Si5 [ No CAS ]
  • 69
  • CHF3O3S*C174H229F12N17O47P5PolS5Si6 [ No CAS ]
  • [ 1546-79-8 ]
  • C176H228F15N17O48P5PolS5Si6 [ No CAS ]
  • 70
  • CHF3O3S*C174H229F12N17O47P5PolS5Si6 [ No CAS ]
  • [ 1546-79-8 ]
  • C176H228F15N17O48P5PolS5Si6 [ No CAS ]
  • 71
  • CHF3O3S*C203H268F15N20O54P6PolS6Si7 [ No CAS ]
  • [ 1546-79-8 ]
  • C205H267F18N20O55P6PolS6Si7 [ No CAS ]
  • 72
  • CHF3O3S*C203H268F15N20O54P6PolS6Si7 [ No CAS ]
  • [ 1546-79-8 ]
  • C205H267F18N20O55P6PolS6Si7 [ No CAS ]
  • 73
  • CHF3O3S*C231H305F18N23O62P7PolS7Si8 [ No CAS ]
  • [ 1546-79-8 ]
  • C233H304F21N23O63P7PolS7Si8 [ No CAS ]
  • 74
  • CHF3O3S*C231H305F18N23O62P7PolS7Si8 [ No CAS ]
  • [ 1546-79-8 ]
  • C233H304F21N23O63P7PolS7Si8 [ No CAS ]
  • 75
  • CHF3O3S*C259H342F21N26O70P8PolS8Si9 [ No CAS ]
  • [ 1546-79-8 ]
  • C261H341F24N26O71P8PolS8Si9 [ No CAS ]
  • 76
  • CHF3O3S*C259H342F21N26O70P8PolS8Si9 [ No CAS ]
  • [ 1546-79-8 ]
  • C261H341F24N26O71P8PolS8Si9 [ No CAS ]
  • 77
  • CHF3O3S*C287H379F24N29O78P9PolS9Si10 [ No CAS ]
  • [ 1546-79-8 ]
  • C289H378F27N29O79P9PolS9Si10 [ No CAS ]
  • 78
  • CHF3O3S*C287H379F24N29O78P9PolS9Si10 [ No CAS ]
  • [ 1546-79-8 ]
  • C289H378F27N29O79P9PolS9Si10 [ No CAS ]
  • 79
  • CHF3O3S*C104H131F3N13O24P2PolS2Si3 [ No CAS ]
  • [ 1546-79-8 ]
  • C106H130F6N13O25P2PolS2Si3 [ No CAS ]
  • 80
  • CHF3O3S*C104H131F3N13O24P2PolS2Si3 [ No CAS ]
  • [ 1546-79-8 ]
  • C106H130F6N13O25P2PolS2Si3 [ No CAS ]
  • 81
  • CHF3O3S*C135H171F6N19O31P3PolS3Si4 [ No CAS ]
  • [ 1546-79-8 ]
  • C137H170F9N19O32P3PolS3Si4 [ No CAS ]
  • 82
  • CHF3O3S*C135H171F6N19O31P3PolS3Si4 [ No CAS ]
  • [ 1546-79-8 ]
  • C137H170F9N19O32P3PolS3Si4 [ No CAS ]
  • 83
  • CHF3O3S*C62H81N5O15PPolSSi2 [ No CAS ]
  • [ 1546-79-8 ]
  • C64H80F3N5O16PPolSSi2 [ No CAS ]
  • 84
  • CHF3O3S*C64H84N6O15PPolSSi2 [ No CAS ]
  • [ 1546-79-8 ]
  • C66H83F3N6O16PPolSSi2 [ No CAS ]
  • 85
  • CHF3O3S*C65H84N8O14PPolSSi2 [ No CAS ]
  • [ 1546-79-8 ]
  • C67H83F3N8O15PPolSSi2 [ No CAS ]
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