Structure of 1260742-02-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1260742-02-6 |
Formula : | C10H10F3NO3 |
M.W : | 249.19 |
SMILES Code : | O=C(OCC)C1=CC=C(N)C(OC(F)(F)F)=C1 |
MDL No. : | MFCD15527570 |
InChI Key : | SRDSPOINRBCMRD-UHFFFAOYSA-N |
Pubchem ID : | 53419483 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P264-P270-P301+P312-P330 |
* 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 |
---|---|---|
With thionyl chloride; for 3h;Reflux; | Intermediate Example Int24.01eth l 4-amino-3-(trifluoromethoxy)benzoateTo a stirred solution of 4-amino-3-(trifluoromethoxy)benzoic acid (5.0 g) in ethanol (100 mL) was added thionyl chloride (2.47 mL) at 0 C. The mixture was heated to reflux for 3 h. The solvent was removed in vacuum. The residue was dissolved in ethyl acetate and the mixture was washed with a half- saturated solution of sodium bicarbonate and with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum, to give 4.81 g of the title compound, that was used for the next step without purification. | |
With thionyl chloride; In ethanol; for 3h;Reflux; | Intermediate Example Int 15.07.01ethyl 4-amino-3-(trifluoromethoxy)benzoate To a stirred solution of 4-amino-3-(trifluoromethoxy)benzoic acid (5.0 g) in ethanol (100 mL) was added thionyl chloride (2.47 mL) at 0 C. The mixture was heated to reflux for 3 h. The solvent was removed in vacuum. The residue was dissolved in ethyl acetate and the mixture was washed with a half- saturated solution of sodium bicarbonate and with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum, to give 4.81 g of the title compound, that was used for the next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate Example Int24.02ethyl 4-bromo-3-(trifluoromethoxy)benzoateTo a stirred solution of Int24.01 (4.8 g) in concentrated aqueous hydrobromic acid (53 mL) was added at 5 C 9.0 mL of a 3 M solution of sodium nitrite. The mixture was stirred for 10 minutes and copper(1 ) bromide (2.76 g) was added. The mixture was stirred for 5 minutes and water (125 mL) was added and the mixture was stirred for 1 h. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gelchromatography gave 4.1 g of the title compound. | ||
Intermediate Example Int 15.07.02ethyl 4-bromo-3-(trifluoromethoxy)benzoateTo a stirred solution of Int 15.07.01 (4.8 g) in concentrated aqueous hydrobromic acid (53 mL) was added at 5 C 9.0 mL of a 3M solution of sodium nitrite. The mixture was stirred for 10 minutes and copper(1 ) bromide (2.76 g) was added. The mixture was stirred for 5 minutes and water (125 mL) was added and the mixture was stirred for 1 h. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 4.1 g of the title compound. | ||
With hydrogen bromide; sodium nitrite;copper(I) bromide; In water; at 5.0℃; for 1h; | Intermediate Example Int24.02eth l 4-bromo-3-(trifluoromethoxy)benzoateTo a stirred solution of Int24.01 (4.8 g) in concentrated aqueous hydrobromic acid (53 mL) was added at 5 C 9.0 mL of a 3M solution of sodium nitrite. The mixture was stirred for 10 min and copper(1 ) bromide (2.76 g) was added. The mixture was stirred for 5 min and water (125 mL) was added and the mixture was stirred for 1 h. The mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 4.1 g of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In ethanol; for 3h;Reflux; | Intermediate Example Int24.01ethyl 4-amino-3-(trifluoromethoxy)benzoateTo a stirred solution of 4-amino-3-(trifluoromethoxy)benzoic acid (5.0 g) in ethanol (100 mL) was added thionyl chloride (2.47 mL) at 0C. The mixture was heated to reflux for 3 h. The solvent was removed in vacuum. The residue was dissolved in ethyl acetate and the mixture was washed with a half- saturated solution of sodium bicarbonate and with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum, to give 4.81 g of the title compound, that was used for the next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75 mg | With potassium tert-butylate; In N,N-dimethyl-formamide; at 20.0℃; | Example 47A Ethyl 4-[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}-3-(trifluoromethoxy)benzoate (0529) (0530) 150 mg (0.38 mmol) of the compound from example 2A and 95 mg (0.38 mmol) of 187 <strong>[1260742-02-6]ethyl 4-amino-3-(trifluoromethoxy)benzoate</strong> were dissolved in 3 ml of 49 DMF. 86 mg (0.76 mmol) of 153 potassium tert-butoxide were added, and the mixture was stirred at RT for 15 min. Thereafter, a further 22 mg (0.19 mmol) of potassium tert-butoxide were added gradually. Stirring of the reaction mixture continued at RT overnight, and then it was purified, without further workup, by means of preparative HPLC (method 6). After the solvent-water mixture had been removed, the residue was dried under reduced pressure overnight. 75 mg (34% of theory, 100% purity) of the 188 title compound were obtained. (0531) LC/MS (Method 1, ESIpos): Rt=1.38 min, m/z=573/575 [M+H]+. |
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