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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. : | 1122-54-9 |
Formula : | C7H7NO |
M.W : | 121.14 |
SMILES Code : | C1=C(C(=O)C)C=CN=C1 |
MDL No. : | MFCD00006433 |
InChI Key : | WMQUKDQWMMOHSA-UHFFFAOYSA-N |
Pubchem ID : | 14282 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | 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 |
---|---|---|
32.8% | With ammonia; potassium hydroxide; In ethanol; water; at 20℃; for 20h; | 4-Acetylpyridine (2.04 g, 16.8 mmol) was added to a solution of <strong>[7310-97-6]2,5-bis(methoxy)benzene-1,4-dicarbaldehyde</strong> (0.80 g, 4.12 mmol) in EtOH (250 mL). KOH pellets (0.93 g, 16.6 mmol) were added in one portion, followed by aqueous NH3 (25%, 15 mL). The reaction mixture was stirred at room temperature for 20 h. The precipitate that formed was collected by filtration, washed with H2O and EtOH, and dried in vacuo over P2O5. Compound 2 was recrystallized from EtOH/CHCl3 and was isolated as a pale yellow solid (0.81 g, 1.35 mmol, 32.8%). Decomp > 320 C. 1H NMR (500 MHz, CDCl3) delta/ppm 8.81 (m, 8H, HA2), 8.09 (m, 8H, HA3), 8.07 (s, 4H, HB3), 7.15 (m, 2H, HC3), 3.92 (s, 6H, HOMe). 13C NMR (126 MHz, CDCl3) ?/ppm 154.8 (CB2), 150.6 (CA2), 148.1 (CC2), 146.1 (CB4), 129.0 (CC1), 121.3 (CB3), 121.2 (CA3), 114.1 (CC3), 56.6 (COMe). IR (solid, cm-1) 3079 (w), 3024 (w), 2831 (w), 1696 (w), 1591 (s), 1558 (w), 1541 (w), 1508 (w), 1496 (w), 1397 (w), 1388 (m), 1208 (w), 1181 (w), 1029 (m), 994 (w), 858 (w), 819 (s), 742 (w), 734 (w), 673 (w), 652 (s), 629 (s), 598 (w). ESI-MS m/z 601.6 [M+H]+ (base peak, calc. 601.2). HR ESI-MS m/z 601.2350 [M+H]+ (base peak, calc. 601.2347). UV-Vis lambda/nm (epsilon/dm3 mol-1 cm-1) (CH2Cl2, 2.5 * 10-5 mol dm-3) 257 (34 300), 316 sh (14 550), 340 sh (11 200). Satisfactory elemental analysis could not be obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With piperidine; for 1h;Heating; | General procedure: A mixture of <strong>[25365-71-3]2-phenyl-1H-indole-3-carboxaldehyde</strong> (1)(1.0 mmol, 0.22 g) and 3- or 4-acetylpyridine (1.0 mmol, 0.1 mL) or2-acetylthiophen (1.3 mmol) and piperidine (0.2 mL) was heatedfor 1 h, then ethanol (1.5 mL), glacial acetic acid and water (1:1)were added dropwise to the resulting red solution until firstappearance cloudiness. The resulting product was filtered off,washed with water and recrystallized from ethanol. In case of 2-thienyl derivative of chalcone, the product obtained was stickymass, triturated with a mixture of petroleum ether and diethylether to afford yellow precipitate, then recrystallized from ethanol. 4.1.2. (E)-3-(2-Phenyl-1H-indol-3-yl)-1-(pyridin-4-yl) prop-2-en-1-one (3a) Yield: 85%. Orange crystals; m.p.: 278-280 C. IR (KBr) νmax/cm-1: 3015 (NH), 1645 (CO), 1H-NMR (DMSO-d6, 400 MHz): δ 7.28-7.31 (m, 2H, indole-C5,6-H), 7.49-7.56 (m, 2H, indole-C4-H,-CHCH-CO), 7.58-7.63 (m, 5H, 2-phenyl-C2,3,4,5,6-H), 7.92 (d,J = 5.0 Hz, 2H, pyridine-C3,5-H), 8.05 (d, J = 15.45 Hz, 1H, -CHCHCO), 8.20 (d, J = 7.00 Hz, 1H, indole-C4-H), 8.78 (d, J= 5.0 Hz, 2H,pyridine-C2,6-H), 12.34 (s, 1H, NH, D2O exchangeable). 13C-NMR(DMSO-d6, 100 MHz): δ 109.44 (indole-C3), 112.35 (indole-C7), 115.54 (indole-C5), 121.26 (indole-C6), 121.50 (pyridine-C3,5), 121.88(indole-C4), 123.45 (2-phenyl-C4), 125.71 (indole-C2), 128.99 (2-phenyl-C2,6), 129.41 (C=C-C=O), 129.75 (2-phenyl-C3,5), 130.70(indole-C3a), 137.00 (2-phenyl-C1), 140.58 (C=C-C=O), 144.70(indole-C7a),146.20 (pyridine-C4), 150.62 (pyridine-C2,6), 188.56(CO). MS EIMS: m/z (calcd) 324.13 (found) 323.90 (M+∘). Anal.Calcd for C22H16N2O: C, 81.46; H, 4.97; N, 8.64. Found: C, 81.63; H,5.15; N 8.79. |