Structure of 160539-04-8
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 160539-04-8 |
Formula : | C10H9N3 |
M.W : | 171.20 |
SMILES Code : | NC1=CN=C(C2=NC=CC=C2)C=C1 |
MDL No. : | MFCD12033465 |
InChI Key : | LRBYBVNTZSPBNA-UHFFFAOYSA-N |
Pubchem ID : | 9877498 |
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 |
---|---|---|
37.8% | With hydroxylamine hydrochloride; triethylamine; In ethanol; water; at 80℃; for 20h; | Method A: The mixture of 66 5-(2,5-dimethyl-1H-pyrrol-1-yl)-2,2'-bipyridine (75.6 mg, 0.3 mmol), 72 hydroxylamine hydrochloride (210.7 mg, 3.0 mmol) and 73 triethylamine (0.084 mL, 0.6 mmol) in 1.4 mL 74 ethanol and 0.6 mL of 75 H2O was stirred at 80C for 20 hours. The mixture was poured over 76 HCl 1M and was washed with diethyl ether. The aqueous layer was neutralized and basified with NaOH 5M and NaOH 2M until obtained pH=9-10 and was extracted with dichloromethane (x3). The different organic layers were collected and were dried. The crude was purified by CombiFlash chromatography column (dichloromethane/dichloromethane:methanol 20%) to afforded the amine derivative (19.6 mg, 37.8%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In diethyl ether; at 100℃; for 4h;Inert atmosphere; Reflux; | A mixture of 2 g (11.7 mmol) of 5-amino-2,2'-dipyridyl, 2.52 g (17.5 mmol, 1.5 gq) of ISOPROPYLIDENE MALONATE, 8.65 g (58.4 mmol,TriethoxymethaneofMixed, and under argon gas protectionUp to 100 Upon heating, a white slurry-like substance appears immediately. After 5 minutes, stop heating, cool and add 50 ml of methanol. The white solid powder is filtered and washed several times with methanol. Drying yielded an intermediate product, pre-pyND, with a yield of 92%. The method of synthesizing pyND from the intermediate is the same as 8mCND, and the yield is 84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43.5% | With tetrakis(triphenylphosphine) palladium(0); In toluene; at 130℃; for 48h;Inert atmosphere; | Method B: To a solution of 55 6-bromopyridin-3-amine (50 mg, 0.29 mmol) in 1.5 mL of dry 63 toluene at room temperature, was added 64 2-(tributylstannyl)pyridine (0.013 mL, 0.35 mmol) dropwise under N2 atmosphere following by the addition of 65 tetrakis(triphenylphosphine)palladium (40.2 mg, 0.03 mmol). The reaction mixture was degassed with nitrogen and was stirred at 130c for two days. The reaction was cooled to room temperature. Next, the mixture was taken up with NaOH 2M and separated with ethyl acetate (x2). The organic layer was washed with brine, was dried with Na2SO4 and the solvent was removed under vacuum. The crude was purified by CombiFlash chromatography column (DCM/DCM:MeOH 20%) to afforded the desired compound (21.6 mg, 43.5 %). 1H-NMR (400 MHz, DMSO-d6): δ = 8.54 (d, 1 H), 8.17 (d, 1 H), 8.08 (d, 1 H), 8.01 (d, 1 H), 7.80 (td, 1 H), 7.25 (m, 1 H), 7.01 (dd, 1 H), 5.65 (s, 2H). HPLC-MS: Rt 2.746; m/z 172.0 (MH+). |
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