Structure of 138964-51-9
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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. : | 138964-51-9 |
Formula : | C9H6BrNO2 |
M.W : | 240.05 |
SMILES Code : | O=C1NC2C=CC(Br)=CC=2C(=O)C1 |
MDL No. : | MFCD29472381 |
InChI Key : | DQFPMEMMMGZBKU-UHFFFAOYSA-N |
Pubchem ID : | 54689446 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
70% | With triethylamine; In ethanol;Reflux; | General procedure: A suspension of 1,6-disubstituted quinoline-2,4-(1H,3H)-diones 1a-d (1 mmol) and dialkyl acetylenedicarboxylates2a,b (2 mmol) in 25 mL absolute ethanol and 0.5 mL oftriethylamine, was gently refluxed for 12-18 h (the reactionwas monitored by TLC). The resulting precipitateswere filtered off, dried and recrystallized from statessolvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With triethylamine; In ethanol;Reflux; | General procedure: A suspension of 1,6-disubstituted quinoline-2,4-(1H,3H)-diones 1a-f (1 mmol) in 10 mL absolute ethanol wasadded to a solution of diethyl acetylenedicarboxylate (2a)(0.170 g, 1 mmol) in 15 mL absolute ethanol and 0.5 mLof triethylamine. The reaction mixture was gently refluxedfor 4-8 h, until the reactants had disappeared (monitoredby TLC). The resulting precipitates of 3a-f were filteredoff and dried. The precipitates were recrystallized fromsuitable solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With triethylamine; In ethanol;Reflux; | General procedure: A suspension of 1,6-disubstituted quinoline-2,4-(1H,3H)-diones 1a-d (1 mmol) and dialkyl acetylenedicarboxylates2a,b (2 mmol) in 25 mL absolute ethanol and 0.5 mL oftriethylamine, was gently refluxed for 12-18 h (the reactionwas monitored by TLC). The resulting precipitateswere filtered off, dried and recrystallized from statessolvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pyridine;Reflux; | General procedure: A 100 cm3 round-bottom flask was flame-dried, a mixtureof 1a-1f (1 mmol), 2 (1 mmol), and 20 cm3 dry pyridinewas refluxed for 8-10 h with stirring (the reaction wasfollowed by TLC analysis). After the reaction’s completion,solvent was then removed under vacuum and theresidue was separated. The solid residue undergoesrecrystallization from the stated solvents to give purecrystals of spiro-compounds 3a-3f |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In propan-1-ol; water; at 125℃; for 8.0h; | Put into 1000kg propanol water and stir in the reactor, add 183kg (1000mol) of saccharin successively, and then added 238.9kg (1000mol) of <strong>[138964-51-9]2-hydroxy-6-bromobenzopyridin-4-one</strong>, heated to 125C under pressure, and reacted under reflux for 8 hours, cool down and reduce pressure, steam to remove 600kg of reclaimed propanol, cool to 5C, and filter after standing for 12 hours to obtain yellow-brown product 4 379.6kg, yield 94%, |