Structure of 1268830-91-6
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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. : | 1268830-91-6 |
Formula : | C9H10FNO3 |
M.W : | 199.18 |
SMILES Code : | O=C(OC)C1=C(F)C=CC(N)=C1OC |
MDL No. : | MFCD20703233 |
InChI Key : | OXIXBTNLXLNCFX-UHFFFAOYSA-N |
Pubchem ID : | 67032764 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
* 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 |
---|---|---|
85% | With pyridine; dmap; In dichloromethane; at 20.0℃; for 14.0833h; | Step C: A 250 mL round bottom flask was charged with a solution of methyl 3-amino-6- fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). To this reaction mixture was added a solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) over a course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, 100 mL saturated aqueous sodium bicarbonate was added followed by stirring for 10 minutes. The aqueous mixture was extracted with 200 mL ethyl acetate (2x). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0-30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)benzoate as an oil (4.914 g, 85%). 1U NMR (400 MHz, DMSO-J6) delta = 9.27 (s, IH), 7.48 (dd, J=9.1, 6.1, IH), 7.09 (t, J=9.0, IH), 3.89 (s, 3H), 3.85 - 3.74 (m, 3H), 3.29 (s, 15H). |
85% | With pyridine;dmap; In dichloromethane; at 20.0℃; for 14.0833h; | A 250 mL round bottom flask was charged with a solution of methyl 3- amino-6-fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). To this reaction mixture was added a solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) over a course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, 100 mL saturated aqueous sodium bicarbonate was added followed by stirring for 10 minutes. The aqueous mixture was extracted with 200 mL ethyl acetate (2x). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0-30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, DMSOd6) delta = 9.27 (s, IH), 7.48 (dd, J=9.1, 6.1, IH), 7.09 (t, J=9.0, IH), 3.89 (s, 3H), 3.85 - 3.74 (m, 3H), 3.29 (s, 15H). |
85% | With pyridine; dmap; In dichloromethane; at 20.0℃; for 14.0h; | A 250 mL round bottom flask was charged with a solution of <strong>[1268830-91-6]methyl 3-amino-6-fluoro-2-methoxybenzoate</strong> (3.656 g, 18.36 mmol) in methylene chloride (100 mL). A solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) was added to the reaction mixture over the course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, saturated aqueous sodium bicarbonate (100 mL) was added followed by stirring for 10 minutes. The aqueous mixture was extracted twice with ethyl acetate (200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0- 30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)- benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, (CD3)2SO) delta = 9.27 (s, 1H), 7.48 (dd, J=9.1, 6.1, 1H), 7.09 (t, J=9.0, 1H), 3.89 (s, 3H), 3.85 - 3.74 (m, 3H), 3.29 (s, 15H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogen;palladium 10% on activated carbon; In methanol; at 20.0℃; under 760.051 Torr; for 60.0h;Inert atmosphere; | Step B: A 250 mL round bottom flask was charged with methyl 6-fluoro-2-methoxy-3- nitrobenzoate (3.37 g, 14.71 mmol) dissolved in methanol (125 mL, 3080 mmol). Nitrogen was passed through the reaction mixture, and 10% palladium on activated carbon (1.3 g, 1.2 mmol) was added. The flask was capped and evacuated and then allowed to stir for 60 hours under an atmosphere of hydrogen at ambient temperature and pressure. The mixture was then filtered through Celite to remove the solid catalyst and washed with methanol (500 mL). The filtrate was concentrated to give methyl 3-amino-6-fluoro-2-methoxybenzoate as an oil (2.95 g, 100%). 1H NMR (400 MHz, DMSO-J6) delta = 6.74-6.84 (m, 2H), 4.98 (s, 2H), 3.85 (s, 3H), 3.68 (s, 3H). |
100% | With hydrogen;palladium 10% on activated carbon; In methanol; at 20.0℃; under 760.051 Torr; for 60.0h; | A 250 niL round bottom flask was charged with methyl 6-fluoro-2- methoxy-3-nitrobenzoate (3.37 g, 14.71 mmol) dissolved in methanol (125 mL, 3080 mmol). Nitrogen was passed through the reaction mixture, and 10% palladium on activated carbon (1.3 g, 1.2 mmol) was added. The flask was capped and evacuated and then allowed to stir for 60 hours under an atmosphere of hydrogen at ambient temperature and pressure. The mixture was then filtered through Celite to remove the solid catalyst and washed with methanol (500 mL). The filtrate was concentrated to give methyl 3-amino-6-fluoro-2-methoxybenzoate as an oil (2.95 g, 100%). 1K NMR (400 MHz, DMSO-d6) delta = 6.74-6.84 (m, 2H), 4.98 (s, 2H), 3.85 (s, 3H), 3.68 (s, 3H). |
100% | With hydrogen;palladium 10% on activated carbon; In methanol; at 20.0℃; under 760.051 Torr; for 60.0h;Inert atmosphere; | A 250 mL round bottom flask was charged with methyl 6-fluoro-2- methoxy-3-nitrobenzoate (3.37 g, 14.71 mmol) dissolved in methanol (125 mL, 3080 mmol). Nitrogen was passed through the reaction mixture, and 10% palladium on activated carbon (1.3 g, 1.2 mmol) was added. The flask was capped and evacuated and then allowed to stir for 60 hours under an atmosphere of hydrogen at ambient temperature and pressure. The mixture was then filtered through Celite to remove the solid catalyst and washed with methanol (500 mL). The filtrate was concentrated to give methyl 3-amino-6-fluoro-2- methoxybenzoate as an oil (2.95 g, 100%). 1H NMR (400 MHz, (CD3)2SO) delta = 6.74-6.84 (m, 2H), 4.98 (s, 2H), 3.85 (s, 3H), 3.68 (s, 3H). |