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CAS No. : | 20075-26-7 | MDL No. : | MFCD00955700 |
Formula : | C5H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XJGYZYRJUUMCAP-UHFFFAOYSA-N |
M.W : | 112.13 | Pubchem ID : | 88359 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 29.38 |
TPSA : | 27.05 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.06 cm/s |
Log Po/w (iLOGP) : | 1.34 |
Log Po/w (XLOGP3) : | -0.11 |
Log Po/w (WLOGP) : | 0.34 |
Log Po/w (MLOGP) : | -0.53 |
Log Po/w (SILICOS-IT) : | 0.21 |
Consensus Log Po/w : | 0.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.8 |
Solubility : | 17.9 mg/ml ; 0.16 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.01 |
Solubility : | 111.0 mg/ml ; 0.988 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.88 |
Solubility : | 14.7 mg/ml ; 0.131 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: With sodium ethanolate In tetrahydrofuran; ethanol at 20℃; for 1 h; Stage #2: at 20℃; |
To a solution of lH-imidazole (40.8 g, 600.00 mmol) in EtOH (1200 niL) under nitrogen was added a solution of sodium ethanolate (40.8 g, 600.00 mmol) in THF (1200 rnL). The resulting solution was stirred for 1 hr at room temperature and concentrated under vacuum. To the residue was added chloro(methoxy) methane (53.4 g, 667.50 mmol) and the resulting solution was stirred for overnight at room temperature. The solids were filtered. The filtrate was concentrated and distilled under reduced pressure, resulted in 40 g (58percent) of l-(methoxym ethyl)- lH-imidazole as white oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | To a solution of lH-imidazole (40.8 g, 600.00 mmol) in EtOH (1200 niL) under nitrogen was added a solution of sodium ethanolate (40.8 g, 600.00 mmol) in THF (1200 rnL). The resulting solution was stirred for 1 hr at room temperature and concentrated under vacuum. To the residue was added chloro(methoxy) methane (53.4 g, 667.50 mmol) and the resulting solution was stirred for overnight at room temperature. The solids were filtered. The filtrate was concentrated and distilled under reduced pressure, resulted in 40 g (58%) of l-(methoxym ethyl)- lH-imidazole as white oil. | |
Step A. 1-Methoxymethyl-1H-imidazole To a solution of 1.06 g of imidazole (15.56 mmol) in 20 ml of THF at 0 C. was added 658 mg (16.45 mmol) of NaH (40% dispersion in oil) and the mixture was stirred at 0 C. for 30 mins.After this time, 1.2 ml (15.7 mmol) of chloromethyl methyl ether were added and the mixture was allowed to warm to room temperature and stirred for 14 h.After this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride, allowed to warm to room temperature, and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated.The residue was purified by chromatography on silica gel (hexanes:EtOAc, 1:1) to give the title compound. 1H-NMR (CDCl3) delta 3.21 (s, 3H), 5.18 (s, 2H), 7.00 (d, J=19 Hz, 2H0, 7.54 (s, 1H). | ||
The starting material was prepared as follows : 1-Methoxymethyl-imidazole To a solution of imidazole (1. 00 g, 14. 7 MMOL) in anhydrous THF (30 ML) AT-78 C was added in portions sodium hydride (0. 88 g of a 60% dispersion in oil, 22. 0 MMOL). The mixture was avowed to warm to room temperature, stirred for 30 minutes, then cooled to- 78 C, and chloromethyl methyl ether (1. 06 ML, 14. 0 MMOL) SLOWLY added. After 2 hours at- 78 C, sat. NAHC03 was added to quench the reaction. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with sat. NAHC03, dried over MgS04, filtered, and concentrated to give 1. 3 G OF an oil, which contained the NaH dispersion oil, displayed AN 1H NMR that matched previous (Zhao, et AL., J. Med. CHEM., VOL. 40, pp. 216-225 (1997)), and was used without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; water; Petroleum ether; | EXAMPLE XXIV Preparation of alpha,alpha-bis(p-fluorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)-imidazole</strong>-2-methanol. To a solution of 11.2 g. (0.1 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> and 13.9 g. (0.12 mol) of N,N,N',N'-tetramethylethylenediamine in 150 ml. of anhydrous tetrahydrofuran 51 ml. (0.12 mol) of a butyllithium solution (20% in n-hexane) was added drop-wise over the course of one hour at -60 C., and under a nitrogen atmosphere. After the addition was completed, stirring was continued for another two hours. The cooling means was then removed and 25.1 g. (0.1 mol) of 4,4'-difluorobenzophenone in 150 ml. of anhydrous tetrahydrofuran were added drop-wise. The reaction mixture was stirred for 6 hours at room temperature and it was then decomposed with 15 ml. of water. The precipitated lithium hydroxide was filtered off and the filtrate was concentrated by distilling off the solvents. 2N Hydrochloric acid was added to the residue, after which the mixture was extracted with diethyl ether. The aqueous phase was made alkaline with 2N sodium hydroxide solution. The precipitate formed was filtered off, washed with water and twice crystallized from a mixture of isopropyl alcohol and petroleum ether (boiling range 40-60 C.). alpha,alpha-Bis(p-fluorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol was obtained. Melting point 133 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; acetic acid; In tetrahydrofuran; diethyl ether; water; acetone; Petroleum ether; | EXAMPLE XV Preparation of alpha,alpha-bis(p-trifluoromethyl-phenyl)imidazole-2-methanol hydrochloride. To a solution of 2.8 g. (0.025 mol) of <strong>[20075-26-7]1-(methoxymethyl)-imidazole</strong> and 3.5 g. (0.03 mol) of N,N,N',N'-tetramethylethylenediamine in 50 ml. of anhydrous tetrahydrofuran a butyllithium solution, prepared from 0.5 g. (0.075 g. at) of lithium and 4.1 g. (0.030 mol) of butyl bromide in 40 ml. of anhydrous diethyl ether, was added drop-wise with stirring at a temperature of -60 C. and under a nitrogen atmosphere. After 2 hours, 8 g. (0.025 mol) of 4,4'-bis(trifluoromethyl)benzophenone in 60 ml. of anhydrous tetrahydrofuran were added at -60 C. The solution was kept standing overnight at room temperature and it was then decomposed with 50 ml. of water and extracted with diethyl ether. The extract was dried over sodium sulphate and the solvent was distilled off. The benzophenone starting material, present in the residue, was dissolved by boiling with petroleum ether (boiling range 40-60 C.) and removed. The residue was then dissolved in a mixture of 75 ml. of acetic acid, 7.5 ml. of water and 75 ml. of concentrated hydrochloric acid, and the solution was refluxed for 5 hours. The liquid was distilled off and the residue was extracted with a mixture of 2 N hydrochloric acid and diethyl ether. The ethereal layer was dried over sodium sulphate. The sodium sulphate was washed with acetone. The solutions in ether and acetone were combined and the solvents were distilled off. The residue was washed with diethyl ether and filtered with suction. There was obtained alpha,alpha-bis(p-trifluoromethyl-phenyl)imidazole-2-methanol hydrochloride. Melting point 210-216 C. (with decomposition). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; In tetrahydrofuran; hydrogenchloride; diethyl ether; chloroform; water; | A. Preparation of 1-(methoxymethyl)-alpha-phenyl-alpha-(m-trifluoromethyl-phenyl)imidazole-2-methanol. Under a nitrogen atmosphere and at a temperature between -60 and -65 C. a butyllithium solution, prepared from 2.04 g. (0.29 g. at) of lithium and 15.8 g. (0.116 mol) of butyl bromide in 130 ml. of anhydrous diethyl ether, was added drop-wise to a solution of 9.8 g. (0.088 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> and 10.2 g. (0.088 mol) of N,N,N',N'-tetramethylethylenediamine in 250 ml. of anhydrous tetrahydrofuran. After 2 hours stirring, a solution of 22 g. (0.088 mol) of 3-(trifluoromethyl)benzophenone in 150 ml. of anhydrous tetrahydrofuran were added dropwise to the reaction mixture at a temperature between -60 and -65 C. The reaction mixture was stirred for one hour at -65 C. and it was then kept standing overnight at room temperature. Then 20 ml. of water were added to the reaction mixture and the solvents were distilled off. The residue was dissolved in dilute hydrochloric acid and the solution was washed with diethyl ether and made alkaline with potassium carbonate. The solid substance formed was filtered off and dissolved in chloroform. The solution was dried over sodium sulphate, the solvent was distilled off and the residue was crystallized from isopropyl alcohol. 1-(Methoxymethyl)-alpha-phenyl-alpha-(m-trifluoromethyl-phenyl)imidazole-2-methanol was obtained. Melting point 152.5-153.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N,N,N,-tetramethylethylenediamine; carbon dioxide; potassium carbonate; In tetrahydrofuran; hydrogenchloride; diethyl ether; chloroform; water; | A. Preparation of 1-(methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol. A butyllithium solution, prepared from 1.02 g. (0.145 g. at.) of lithium and 7.9 g. (0.058 mol) of butyl bromide in 70 ml. of anhydrous diethyl ether, was added drop-wise at -60 C. to -65 C. under a nitrogen atmosphere to a solution of 4.9 g. (0.044 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> and 3.1 g. (0.044 mol) of N,N,N',N'-tetramethylethylenediamine in 125 ml. of anhydrous tetrahydrofuran. The reaction mixture was kept standing for 2 hours at -60 to -65 C. and then 11 g. (0.044 mol) of 4-(trifluoromethyl)benzophenone, dissolved in 75 ml. of anhydrous tetrahydrofuran, were added drop-wise. The temperature was maintained at -65 C. for one hour and then the reaction mixture was allowed to attain room temperature overnight. 10 ml. of water and solid carbon dioxide were added and the solvent was distilled off. The residue was dissolved in dilute hydrochloric acid, the solution was washed with diethyl ether and made alkaline with potassium carbonate. The solid substance formed was filtered off and dissolved in chloroform. The solution was washed with water, dried over sodium sulphate and concentrated by evaporation of the solvent. The residue was crystallized from isopropyl alcohol. 1-(Methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol was obtained. Melting point 158-159 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; diethyl ether; hexane; water; Petroleum ether; | Preparation of 1-(methoxymethyl)-alpha,alpha-bis(p-trifluoromethylphenyl)imidazole-2-methanol 9.1 Ml. (0.015 mol) of n-butyl lithium solution (15% in n-hexane) were added dropwise with stirring at -60 C. and under a nitrogen atmosphere to a solution of 1.7 g (0.015 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> and 1.8 g (0.015 mol) of N,N,N',N'-tetramethylethylenediamine in 75 ml. of anhydrous tetrahydrofuran. Stirring was continued for 1.5 hours and then 2.9 g (0.0091 mol) of 4,4'-bis(trifluoromethyl)benzophenone in 50 ml. of anhydrous tetrahydrofuran were added dropwise under the same conditions, which made the colour change from light red into very dark brown. The reaction mixture was kept standing overnight at room temperature and it was then decomposed by addition of 40 ml. of water. The mixture was extracted with diethyl ether and the extract was concentrated. The residue was extracted with a mixture of 2 N hydrochloric acid and diethyl ether. The ethereal phase was dried over sodium sulphate and the ether was distilled off. The residue was boiled a few times with petroleum ether (boiling range 40-60 C.) to remove ketone starting material and it was then once crystallized from a mixture of toluene and petroleum ether (boiling range 28-40 C.) twice from petroleum ether (boiling range 100-140 C.). 1-(Methoxymethyl)-alpha,alpha-bis(p-trifluoromethylphenyl)imidazole-2-methanol was obtained. Melting point 160-161 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; chloro-trimethyl-silane; triethylamine; In tetrahydrofuran; hexane; dichloromethane; ammonium chloride; toluene; | EXAMPLE XVIII Preparation of alpha,alpha-bis(p-chlorophenyl)-<strong>[20075-26-7]1-methoxymethylimidazole</strong>-2-methanol. To a solution of 22.4 g. (0.2 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> in 150 ml. of anhydrous tetrahydrofuran 92 ml. (0.2 mol) of butyllithium solution (20% in hexane) was added drop-wise with stirring under a nitrogen atmosphere at -60 C. The reaction mixture was stirred for 2 hours, after which anhydrous carbon dioxide gas was introduced. After being stirred for one hour, the mixture was poured onto solid carbon dioxide. The lithium salt of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-carboxylic acid precipitated. The salt was filtered off and washed with diethyl ether. To a suspension of 16.2 g. (0.1 mol) of the lithium salt and 35 g. (0.35 mol) of triethylamine in 150 ml. of anhydrous dichloromethane 48.8 g. (0.45 mol) of chlorotrimethylsilane was added drop-wise with stirring under a nitrogen atmosphere. The mixture was stirred for 20 hours, then 300 ml. of anhydrous toluene was added and stirring was continued for another hour. The lithium salts formed were filtered off and the filtrate was concentrated by evaporation of the solvents. The residue, containing the trimethylsilyl ester of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-carboxylic acid, was dissolved in 100 ml. of anhydrous tetrahydrofuran and added dropwise to a refluxing solution of a Grignard compound prepared from 8.1 g. (0.3 g. at.) of magnesium and 57.5 g. (0.3 mol) of 4-bromo-1-chlorobenzene in 150 ml. of anhydrous tetrahydrofuran. The mixture was refluxed for one hour and then decomposed in an ammonium chloride solution. The precipitate was filtered off and the filtrate was extracted with diethyl ether. The ethereal phase was extracted with 2 N hydrochloric acid and the acid extract was made alkaline with ammonia and extracted with diethyl ether. The ethereal extract was dried over sodium sulphate and the solvent was distilled off. The residue was twice crystallized from isopropyl alcohol. alpha,alpha-Bis-(p-chlorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol was obtained. Melting point 145-146 C. The compound was converted into alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol as described in Example VII B. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; ammonia; In tetrahydrofuran; diethyl ether; hexane; water; Petroleum ether; | A. Preparation of alpha,alpha-bis(2,4-dichlorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol To a solution of 7.6 g (0.0676 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> and 8.1 g (0.0676 mol) of N,N,N',N'-tetramethylethylenediamine in 150 ml of anhydrous tetrahydrofuran were added dropwise under a nitrogen atmosphere at -60 C., 43 ml. (0.070 mol) of n-butyl lithium solution (15% in n-hexane). The solution was stirred at -60 C. for one hour. Then 23 g (0.0676 mol) of 2,2',4,4'-tetrachlorobenzophenone (prepared as described by S. D. Wilson and Yuan Ying Cheng, J. Org. Chem. 5, 223-6 (1940)) in 150 ml. of anhydrous tetrahydrofuran were added dropwise. The solution was stirred another hour at -60 C. and one night at room temperature. The reaction mixture was decomposed with 100 ml. of water and extracted with diethyl ether. The organic phase was dried over sodium sulphate and concentrated and the residue was extracted with a mixture of 2N hydrochloric acid and diethyl ether on which a solid substance was formed, which was crystallized from a mixture of isopropyl alcohol and diethyl ether. The product appeared to be the hydrochloride of the desired compound, contaminated with the compound without methoxymethyl group. Ammonia and diethyl ether were added to liberate the free base. The ethereal phase was concentrated and the residue was four times crystallized from a mixture of isopropyl alcohol and petroleum ether (boiling range 60-80 C.). alpha,alpha-Bis-(2,4-dichlorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol was obtained. Melting point 145.5-146 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; water; | A. Preparation of alpha-(2,4-dichlorophenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol This compound was prepared by the procedure described in Example XXVII B, using the following materials: 9.8 g (0.088 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>, 10.4 g (0.09 mol) of N,N,N',N'-tetramethylethylenediamine, 100 ml. of anhydrous tetrahydrofuran, 62 ml. (0.10 mol) of 15% butyl lithium in n-hexane, 22.6 g (0.09 mol) of 2,4-dichlorobenzophenone in 100 ml. of anhydrous tetrahydrofuran. The reaction mixture was decomposed with 75 ml. of water. The solid matter formed was filtered off and the aqueous phase of the filtrate was discarded. The organic phase was concentrated. The residue appeared to be identical to the solid matter filtered off. The combined solid substances were crystallized from isopropyl alcohol. alpha-(2,4-Dichlorophenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol was obtained. Melting point 161-161.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; water; | EXAMPLE XXVI Preparation of alpha-(o-tert.-butylphenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol. Under a nitrogen atmosphere and at -60 C., 38 ml. (0.08 mol) of a butyllithium solution (20% in n-hexane) were added drop-wise over the course of 45 minutes to a mixture of 9.6 g. (0.08 mol) of N,N,N',N'-tetramethylethylenediamine and 7 g. (0.06 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> in 100 ml. of anhydrous tetrahydrofuran. The mixture was stirred for another two hours under the same conditions and then 16 g (0.0675 mol) of o-tert.-butylbenzophenone in 100 ml. of anhydrous tetrahydrofuran were added dropwise. After the addition was completed, the mixture was stirred for 2 hours at -60 C., and one hour at room temperature. The mixture was decomposed with 5 ml. of water, the precipitate was filtered off and the filtrate was dried over sodium sulphate and concentrated. The solid residue was crystallized from isopropyl alcohol. alpha-(o-tert.-Butylphenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol was obtained. Melting point 149-150 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; diethyl ether; hexane; water; | A. Preparation of alpha-(2,4-dichlorophenyl)-alpha-(p-fluorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol At -60 C. and under a nitrogen atmosphere, 44 ml. (0.072 mol) of n-butyl lithium (15% solution in n-hexane) was added dropwise under stirring to a solution of 7.8 g (0.07 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong> and 8.1 g (0.072 mol) of N,N,N',N'-tetramethylethylenediamine in 100 ml of anhydrous tetrahydrofuran. The mixture was stirred for one hour and then 18.9 g (0.070 mol) of 2,4-dichloro-4'-fluorobenzophenone in 100 ml of anhydrous tetrahydrofuran were added at -60 C. The solution was stirred for one hour at -60 C. and kept standing overnight at room temperature. Then 50 ml of water were added and the solid matter formed was filtered off. The filtrate was extracted with tetrahydrofuran and diethyl ether. The organic phase was dried over sodium sulphate and the solvents were distilled off. Diethyl ether was added to the semisolid residue and the solid matter was filtered off. This product was combined with the solid matter obtained after the addition of water. The substance was twice crystallized from acetone with a small amount of dimethylformamide. alpha-(2,4-Dichlorophenyl)-alpha-(p-fluorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol was obtained. Melting point 179 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; diethyl ether; hexane; water; | A. Preparation of alpha-(p-tert.-butylphenyl-alpha-(p-chlorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol This compound was prepared by the procedure described in Example XXVII B, using the following materials: 11.2 g (0.1 mol) of <strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>, 13.35 g (0.115 mol) of N,N,N',N'-tetramethylethylenediamine in 250 ml. of anhydrous tetrahydrofuran, 70 ml. (0.115 mol) of 15% butyl lithium in n-hexane, 27.3 g (0.1 mol) of 4-tert.-butyl-4'-chlorobenzophenone (F. A. Vingiello and C. K. Bradsher, J. Am. Chem. Soc. 71, 3572 (1949)) in 150 ml. of anhydrous tetrahydrofuran. After decomposition of the reaction mixture with 25 ml. of water, the organic phase was separated off, washed thrice with an aqueous sodium chloride solution and dried over sodium sulphate. The solvent was distilled off and the residue was suspended in a small amount of cold diethyl ether. The solid substance was filtered off and twice crystallized from acetone. alpha-(p-tert.-Butylphenyl)-alpha-(p-chlorophenyl)-<strong>[20075-26-7]1-(methoxymethyl)imidazole</strong>-2-methanol was obtained. Melting point 162-163 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step B. N-Methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(1-methoxymethyl-1H-imidazol-2-yl)-ethyl]-phenyl}-benzenesulfonamide To a solution of 55 mg (0.49 mmol) of <strong>[20075-26-7]1-methoxymethyl-1H-imidazole</strong> in 5 ml of THF at -78 C. was added 0.20 ml (0.50 mmol) of a 2.5 M solution of n-butyllithium in hexanes and the resultant mixture was stirred at -78 C. for 30 mins.After this time, a solution of 160 mg (0.47 mmol) of N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide (Example 22, Step A) in 2 ml of THF was added and the resultant mixture stirred at -78 C. for a further 2 h, and then at room temperature for 14 h.After this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated.The residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1) to give the title compound. 1H-NMR (CDCl3) delta 3.09 (s, 3H), 3.19 (s, 3H), 4.90 (s, 2H), 5.16 (brs, 1H), 7.07-7.16 (m, 4H), 7.42-7.62 (m, 7H).Mass Spectrum (CI+) m/e=456.1 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
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11% | The title compound was prepared as follows. To a solution of 1-methoxymethyl- imidazole (216 mg, 1. 95 MMOL) in dry THF (20 mi) AT-78 C was added slowly a solution of t- butyllithium (2. 4 ml of 1. 7 M in THF). After 20 minutes, ZNCI2 (663 mg, 4. 86 MMOL) was added, the mixture was allowed to warm to room temperature and stirred for another 60 min. 1- 4-AMINO-2- [1- (6-CHLORO-PYRIDINE-3-SULFONYL)-PIPERIDIN-4-YLAMINO]-THIAZOL-5-YL}-1-PHENYL- methanone (Example F21 ; 200 mg, 0. 390 MMOL) AND TETRAKIS (TRIPHENYLPHOSPHINO) PALLADIUM (0) (Pd (Ph3P) 4 ; 12 mg, 0. 013 MMOL) were added and the mixture REFLUXED under argon for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with 0. 1 NAOH, dried over MGS04, filtered, and concentrated. The resultant solid was dissolved in a solution of 38% HCI (10 ML), ethanol (15 MI), and H20 (15 ml) and REFLUXED for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with sat. NaHCO3, dried over MGS04, filtered, concentrated, and purified via preparative HPLC. The concentrate from fractions was dissolved in EtOAc, washed with sat NAHC03, dried over MGS04, filtered, and concentrated. The resultant solid was placed in acetonitrile (30 ML), water (90 ML), and 38% HCI (0. 5 mL) and evaporated to give 26 mg of white powder in 11 % yield. 'H NMR (CD30D) : 8 9. 13 (d1H, J=2. 5 Hz), 8. 44 (dd, 1H, J=2. 5, 8. 3 Hz), 8. 23 (d, 1H, J=8. 3 Hz), 7. 78 (s, 2H), 7. 50-7. 40 (m, 1H), 7. 08-6. 97 (m, 2H), 4. 02-3. 90 (m, 3H), 2. 98-2. 87 (m, 2H), 2. 37-2. 13 (m, 2H), 1. 96-1. 78 (m, 2H). ESIMS (MH+) : 546. Anal. Calcd for C23H2, F2N703S2 O 2. 4 HCI * 1. 0 H2O # 0. 5 EtOAc : C, 43. 19 ; H, 4. 26 ; N, 14. 10 ; S, 9. 23. Found : C, 42. 85 ; H, 4. 67 ; N, 14. 50 ; S, 9. 27. |
Tags: 20075-26-7 synthesis path| 20075-26-7 SDS| 20075-26-7 COA| 20075-26-7 purity| 20075-26-7 application| 20075-26-7 NMR| 20075-26-7 COA| 20075-26-7 structure
[ 19213-72-0 ]
Ethyl 1H-imidazole-1-carboxylate
Similarity: 0.67
[ 79917-88-7 ]
1,3-Dimethyl-1H-imidazol-3-ium chloride
Similarity: 0.62
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