Structure of 101906-05-2
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 101906-05-2 |
Formula : | C9H7F3O3 |
M.W : | 220.15 |
SMILES Code : | FC(C1=CC=C(C(C(O)O)=O)C=C1)(F)F |
MDL No. : | MFCD08705869 |
InChI Key : | XFHIKQUDYLBELB-UHFFFAOYSA-N |
Pubchem ID : | 2783285 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-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 |
---|---|---|
15% | With acetic acid;Reflux; | General procedure: The mixture of 3 (2.5 mmol) and the appropriate phenylglyoxal hydrate (2.5 mmol) in glacialacetic acid (6 mL) was stirred at reflux for 23-31 h. After standing at room temperature, the precipi-tatewas filtered off and dried. A final purification was described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With acetic acid; for 30h;Reflux; | General procedure: A mixture of the appropriate aminoguanidine 19-26 (1 mmol) and phenylglyoxal hydrate (1 mmol)in glacial acetic acid (2.5 mL) was refluxed with stirring for 24-45 h. The solid of the compound was obtained either after stirring overnight at room temperature, or after additional stirring on an ice bathfor 12 h (compds. 30-31, 42-44, 47). The formed precipitate was collected by filtration, washed withglacial acetic acid (2 x 1 mL) and dried. The final products 27-60 were purified as described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With acetic acid; for 45h;Reflux; | General procedure: A mixture of the appropriate aminoguanidine 19-26 (1 mmol) and phenylglyoxal hydrate (1 mmol)in glacial acetic acid (2.5 mL) was refluxed with stirring for 24-45 h. The solid of the compound was obtained either after stirring overnight at room temperature, or after additional stirring on an ice bathfor 12 h (compds. 30-31, 42-44, 47). The formed precipitate was collected by filtration, washed withglacial acetic acid (2 x 1 mL) and dried. The final products 27-60 were purified as described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; for 33h;Reflux; | General procedure: A mixture of the appropriate aminoguanidine 19-26 (1 mmol) and phenylglyoxal hydrate (1 mmol)in glacial acetic acid (2.5 mL) was refluxed with stirring for 24-45 h. The solid of the compound was obtained either after stirring overnight at room temperature, or after additional stirring on an ice bathfor 12 h (compds. 30-31, 42-44, 47). The formed precipitate was collected by filtration, washed withglacial acetic acid (2 x 1 mL) and dried. The final products 27-60 were purified as described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With acetic acid; for 33h;Reflux; | General procedure: A mixture of the appropriate aminoguanidine 19-26 (1 mmol) and phenylglyoxal hydrate (1 mmol)in glacial acetic acid (2.5 mL) was refluxed with stirring for 24-45 h. The solid of the compound was obtained either after stirring overnight at room temperature, or after additional stirring on an ice bathfor 12 h (compds. 30-31, 42-44, 47). The formed precipitate was collected by filtration, washed withglacial acetic acid (2 x 1 mL) and dried. The final products 27-60 were purified as described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With acetic acid; for 33h;Reflux; | General procedure: A mixture of the appropriate aminoguanidine 19-26 (1 mmol) and phenylglyoxal hydrate (1 mmol)in glacial acetic acid (2.5 mL) was refluxed with stirring for 24-45 h. The solid of the compound was obtained either after stirring overnight at room temperature, or after additional stirring on an ice bathfor 12 h (compds. 30-31, 42-44, 47). The formed precipitate was collected by filtration, washed withglacial acetic acid (2 x 1 mL) and dried. The final products 27-60 were purified as described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With acetic acid; for 33h;Reflux; | General procedure: A mixture of the appropriate aminoguanidine 19-26 (1 mmol) and phenylglyoxal hydrate (1 mmol)in glacial acetic acid (2.5 mL) was refluxed with stirring for 24-45 h. The solid of the compound was obtained either after stirring overnight at room temperature, or after additional stirring on an ice bathfor 12 h (compds. 30-31, 42-44, 47). The formed precipitate was collected by filtration, washed withglacial acetic acid (2 x 1 mL) and dried. The final products 27-60 were purified as described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dichloro-ethane; at 25℃; for 0.25h;Inert atmosphere; | General procedure: A mixture of glyoxal monohydrate derivative (0.5 mmol, 1.0 equiv), coumarin derivative (0.5 mmol, 1.0 equiv) and amine (0.5 mmol, 1.0 equiv) were stirred in 3mL DCE at room temperature for 15 mins. Then, malononitrile (0.5 mmol, 1.0 equiv) and Et3N (0.5 mmol, 1.0 equiv) were added into the above mixture, the reaction was further stirred for another 8 hrs, the reaction was carried out under nitrogen protection. Afterthe completeness of the reaction, the reaction mixture was diluted with 10 mL DCM. The above mixture was then washed with 5 mL water, the organic extracts were collected and concentrated. Purification of the crude product was carried out by chromatography (silica gel, methanol : dichloromethane = 1 : 30) to afford 2a-2y as desired products. |