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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. : | 63927-22-0 |
Formula : | C9H6BrN |
M.W : | 208.06 |
SMILES Code : | C1=NC=CC2=CC=CC(=C12)Br |
MDL No. : | MFCD04973298 |
InChI Key : | DPRIHFQFWWCIGY-UHFFFAOYSA-N |
Pubchem ID : | 9859134 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
59% | To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 2.46 g (11.8 mmol) <strong>[63927-22-0]8-bromoisoquinoline</strong>, 1.68 mL (14.1 mmol) benzyl bromide, and 10 mL ethanol. The solution was heated at reflux for 6 hr, cooled, and evaporated. The oil was dissolved in 50 mL methanol, and 1.73 g (27.6 mmol) sodium cyanoborohydride was added. The solution was stirred at room temperature for 5 days, then diluted with water and extracted with three portions of ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate to afford 1.98 g (59percent) of an oil. 1H-NMR (delta, CDCl3): 2.68 (m, 2H), 2.88 (m, 2H), 3.68 (m, 2H), 3.75 (m, 2H), 7.0-7.1 (m, 2H), 7.2-7.4 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In sulfuric acid; | 8-bromoisoquinoline (24). To 7.0 mL (60.0 mmol) 2-bromobenzaldehyde (23) was added 10.0 mL (69.0 mmol) aminoacetaldehyde diethyl acetal. After 3 h at 100° C., the reaction mixture was cooled to room temperature and the layers separated. The organic layer was purified by vaccum distillation to give 15.89 g bromobenzalaminoacetal (b.p. 141-148° C. at approximately 1 mm Hg). To 143 g concentrated sulfuric acid at 0° C. was added 15.89 g bromobenzalaminoacetal. With mechanical stirring, the resulting mixture was added in portions over 5 min to 20 g phosphoric anhydride in 10 g concentrated sulfuric acid maintained at 160° C. After 25 min at 160° C., the reaction mixture was cooled, poured onto ice and washed with 300 mL ethyl ether. The aqueous layer was basified with solid NaOH to pH=10 and extracted with EtOAc repeatedly. The combined EtOAc layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (75*110 mm silica gel, linear gradient 0.5-3percent (10percent NH4H:MeOH):CH2CI2) produced 24. 1H NMR (CDCl3, 400 MHz) 89.627 (s, 1H, ArH); 8.622 (d, 1H, J=5.67 Hz, ArH); 7.858 (dd, 1H, J=0.87, 7.45 Hz, ArH); 7.799 (d, 1H, J=8.32 Hz, ArH); 7.631 (d, 1H, J=5.76 Hz, ArH); 7.538 (dd, 1H, J=7.50, 8.23 Hz, ArH); MS (Electrospray): m/z 207.9, 209.0 (M+H, 79Br, 81Br). |