Structure of 1442461-73-5
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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. : | 1442461-73-5 |
| Formula : | C16H17BO6 |
| M.W : | 316.11 |
| SMILES Code : | O=C(C1=CC2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2OC1=O)O |
| English Name : | 2-Oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-chromene-3-carboxylic acid |
| MDL No. : | MFCD34186898 |
| InChI Key : | ROYLDHSKPCMDCZ-UHFFFAOYSA-N |
| Pubchem ID : | 139269705 |
* 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 |
|---|---|---|
| Multi-step reaction with 4 steps 1: sodium hydroxide / methanol; water / 24 h / 20 °C 2: boron trifluoride diethyl etherate 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C | ||
| Multi-step reaction with 4 steps 1: sodium hydroxide / methanol; water / 24 h / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C | ||
| Multi-step reaction with 5 steps 1: sodium hydroxide / methanol; water / 24 h / 20 °C 2: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere; Cooling with ice 3: triethylamine / dichloromethane / 3.67 h / 0 - 20 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C | ||
| Multi-step reaction with 3 steps 1: boron trifluoride diethyl etherate 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C | ||
| Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere; Cooling with ice 2: triethylamine / dichloromethane / 3.67 h / 0 - 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With trifluoroacetic acid In dichloromethane at 20℃; for 1h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 48.33 h / 20 °C / Inert atmosphere; Cooling with ice 2: trifluoroacetic acid / dichloromethane / 18 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 48.33 h / 20 °C / Inert atmosphere; Cooling with ice 2: trifluoroacetic acid / dichloromethane / 18 h / 20 °C 3: triethylamine / isopropyl alcohol / 24 h / 85 °C / Sealed tube |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 48.3333h; Inert atmosphere; Cooling with ice; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 5 steps 1: piperidine / acetonitrile / 48 h / 20 °C 2: sodium hydroxide / methanol; water / 24 h / 20 °C 3: boron trifluoride diethyl etherate 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C | ||
| Multi-step reaction with 5 steps 1: piperidine / acetonitrile / 48 h / 20 °C 2: sodium hydroxide / methanol; water / 24 h / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C | ||
| Multi-step reaction with 6 steps 1: piperidine / acetonitrile / 48 h / 20 °C 2: sodium hydroxide / methanol; water / 24 h / 20 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere; Cooling with ice 4: triethylamine / dichloromethane / 3.67 h / 0 - 20 °C 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 6: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 3.67 h / 0 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 12 h / Schlenk technique; Inert atmosphere; Heating 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 8.8 % | Stage #1: 2-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2H-chromen-3-carboxylic acid With dmap In dichloromethane at 20℃; Inert atmosphere; Stage #2: 4-(1-(4-(butylthio)-7-(ethyl(2-methoxy-2-oxoethyl)amino)-2-oxo-2H-chromen-3-yl)-3-ethoxy-3-oxoprop-1-en-2-yl)-1-(2-hydroxyethyl)pyridin-1-ium iodide With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere; | 2 Example 2.Synthetic probe 1-(2-((7-boronic acid-2-oxo-2H-chromene-3-carbonyl)oxy)ethyl)-4-(1-(4-(butylthio))-2-oxo-3H-chromene-3-carbonyl)-7-(ethyl(2-methoxy-2-oxoethyl)amino)-2-oxo-2H-chromen-3-yl)-3-ethoxy-3-oxoprop-1 -en-2-yl)pyridin-1-iodide Under argon protection conditions,2-Oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-2H-chromene-3-carboxylic acid (90.7 mg , 287.1 μmol) and 4-dimethylaminopyridine (3.5 mg, 27.7 μmol) were added to 8 mL of anhydrous dichloromethane.Stir at room temperature for 20 minutes.Then 4-(1-(4-(butylthio)-7-(ethyl(2-methoxy-2-oxyethyl)amino)-2-oxo-2H-chromen-3-yl )-3-ethoxy-3-oxoprop-1-en-2-yl)-1-(2-hydroxyethyl)pyridin-1-iodide(200.0 mg, 287.1 μmol)and 1-ethyl-(3-dimethylaminopropyl)carbodiimide (66.1 mg, 344.5 μmol) were added to the above reaction solution at one time.The reaction was continued with stirring for 6 hours under argon protection.After the TLC monitoring reaction is completed, add appropriate amounts of methylene chloride and water, and separate the liquids.The organic layer was washed three times and concentrated to obtain crude product.Purification by column chromatography yielded 23.0 mg of red solid, with a yield of 8.8%. |
| 8.8 % | Stage #1: 2-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2H-chromen-3-carboxylic acid With dmap In dichloromethane at 20℃; Inert atmosphere; Stage #2: 4-(1-(4-(butylthio)-7-(ethyl(2-methoxy-2-oxoethyl)amino)-2-oxo-2H-chromen-3-yl)-3-ethoxy-3-oxoprop-1-en-2-yl)-1-(2-hydroxyethyl)pyridin-1-ium iodide With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere; | 2 Example 2.Synthetic probe 1-(2-((7-boronic acid-2-oxo-2H-chromene-3-carbonyl)oxy)ethyl)-4-(1-(4-(butylthio))-2-oxo-3H-chromene-3-carbonyl)-7-(ethyl(2-methoxy-2-oxoethyl)amino)-2-oxo-2H-chromen-3-yl)-3-ethoxy-3-oxoprop-1 -en-2-yl)pyridin-1-iodide Under argon protection conditions,2-Oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-2H-chromene-3-carboxylic acid (90.7 mg , 287.1 μmol) and 4-dimethylaminopyridine (3.5 mg, 27.7 μmol) were added to 8 mL of anhydrous dichloromethane.Stir at room temperature for 20 minutes.Then 4-(1-(4-(butylthio)-7-(ethyl(2-methoxy-2-oxyethyl)amino)-2-oxo-2H-chromen-3-yl )-3-ethoxy-3-oxoprop-1-en-2-yl)-1-(2-hydroxyethyl)pyridin-1-iodide(200.0 mg, 287.1 μmol)and 1-ethyl-(3-dimethylaminopropyl)carbodiimide (66.1 mg, 344.5 μmol) were added to the above reaction solution at one time.The reaction was continued with stirring for 6 hours under argon protection.After the TLC monitoring reaction is completed, add appropriate amounts of methylene chloride and water, and separate the liquids.The organic layer was washed three times and concentrated to obtain crude product.Purification by column chromatography yielded 23.0 mg of red solid, with a yield of 8.8%. |