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CAS No. : | 67491-43-4 | MDL No. : | MFCD06637688 |
Formula : | C12H6N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IUMFOUVCDJGKNS-UHFFFAOYSA-N |
M.W : | 206.20 | Pubchem ID : | 10442958 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 56.9 |
TPSA : | 73.36 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.9 cm/s |
Log Po/w (iLOGP) : | 1.83 |
Log Po/w (XLOGP3) : | 0.92 |
Log Po/w (WLOGP) : | 1.89 |
Log Po/w (MLOGP) : | -0.4 |
Log Po/w (SILICOS-IT) : | 2.41 |
Consensus Log Po/w : | 1.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.19 |
Solubility : | 1.34 mg/ml ; 0.0065 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.05 |
Solubility : | 1.85 mg/ml ; 0.00899 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.35 |
Solubility : | 0.00925 mg/ml ; 0.0000449 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.09 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
88% | With trichlorophosphate for 61h; ultrasonication; | |
56.2% | With pyridine; thionyl chloride at 100℃; for 16h; | |
With thionyl chloride In pyridine; dichloromethane | 4 EXAMPLE 4: A suspension of 4.73 g (0.0195 mol) of 4,4'-dicarbamoyl-2,2'-bipyridine [J. Am. Chem. Soc. 80. 2745 (1958)] and 5.67 g (0.0476 mol) of thionyl chloride in 30 ml of pyridine is stirred for 16 hours at 100°. After cooling, the reaction mixture is diluted with 100 ml of methylene chloride, filtered and concentrated to dryness by evaporation. The residue is then chromatographed with methylene chloride over silica gel. In this manner, 4,4'-dicyano-2,2'-bipyridine is obtained in the form of white crystals having a melting point of 238°-240°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Raney nickel 2: oxidation 4: ammonia 5: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: oxidation 3: ammonia 4: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: ammonia 3: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ammonia 2: 88 percent / trichlorooxophosphorus / 61 h / ultrasonication |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: MeONa / 5 h / Heating 2: NH4Cl, NH3 / methanol; ethanol / 1 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride; sodium methylate In hydrogenchloride; methanol; acetic acid | 4 EXAMPLE 4: EXAMPLE 4: 4,4'-diamidino-2,2'-bipyridine dihydrochloride 0.5 m of 1.1N sodium methoxide in absolute methanol is added to a suspension of 1.2 g (0.0058 mol) of 4,4'-dicyano-2,2'-bipyridine in 48 ml of absolute methanol and the whole is boiled for 5 hours under reflux. 0.05 M of glacial acetic acid, 0.72 g (0.0134 mol) of ammonium chloride and 10 ml of 4.6N methanolic ammonia solution are then added to the solution while it is still warm and the whole is boiled for a further one hour. The cooled reaction mixture is concentrated by evaporation, taken up in 60 ml of 0.1N hydrochloric acid, filtered and applied to a column of 250 ml of Amberlite ER 180 adsorber resin. Washing is effected with distilled water and 5 ml fractions are collected. Fractions 14-21 are combined and concentrated by evaporation and the residue is crystallized from a small amount of water to give the title compound; m.p. >280°. The starting compound is prepared as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran under nitrogen;; removal of solvent under vacuum; washing (CHCl3); drying (vacuum); recrystd. (CH2Cl2/ light petroleum); elem. anal.;; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In tetrahydrofuran according to Baxter et al., J. Chem. Soc. Dalton Trans. (1992), 3015; slight excess of norbornadiene complex; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In tetrahydrofuran according to Baxter et al., J. Chem. Soc. Dalton Trans. (1992), 3015; slight excess of norbornadiene complex; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With silver nitrate In N,N-dimethyl-formamide other Radiation; Ru complex, ligand and AgNO3 dissolved in DMF, refluxed under microwavesfor 2 h; cooled to room temp., filtered, evapd., EtOH added, pptd. (aq. NH4PF6), sepd., washed (Et2O), dried (vac.), chromd. (silica, MeCN), crystd. fromMeOH/H2O; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With palladium 10% on activated carbon for 24h; Inert atmosphere; Reflux; | |
7 %Spectr. | With 1,10-Phenanthroline; silver(I) acetate; palladium diacetate; Trimethylacetic acid In toluene at 140℃; for 18h; Inert atmosphere; | 4 Under a nitrogen atmosphere, palladium acetate (11.2 mg, 0.05mmol), 1, 10 - phenanthroline (49.6 mg, 0.25mmol), silver acetate (250 mg, 1.5mmol), (1 ml) was suspended in pyridine (51.1 mg, 0.5mmol) pivalic acid, stirred at 140 °C 26 hours. After the reaction mixture was cooled to room temperature, the insoluble matter was removed by filtration over celite, methylene chloride (10 ml) was washed. The filtrate was concentrated under reduced pressure, 1, 1, 2, 2 - tetrachloroethane (15.8 μl, 0.15mmol) was added as an internal standard substance was obtained residue,1H NMR (88%) yield was calculated based oxidizing agent. (Methylene chloride/hexane=5/95) to give a residue for a thin layer chromatography analysis, the subject compound (quantitative value NMR 89%, 80% isolated yield) was obtained as a white powder 93.1 mg.The same treatment as in Example 1-1 was carried out except that treatment was carried out under the conditions shown in Table 4 below.The results are shown in Table 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,2’-bipyridine-4,4’-dicarbonitrile; lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 96h; Stage #2: chloro-trimethyl-silane In toluene for 12h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate In 1,3,5-trimethyl-benzene for 12h; Inert atmosphere; Reflux; | |
45% | With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate In 1,3,5-trimethyl-benzene at 170℃; for 17h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium hydroxide In ethyl methyl ether for 12h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In chloroform for 7h; Inert atmosphere; Darkness; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: [Ir(2-(benzo[b]thiophen-2-yl)-pyridine)2(triphenylphosphine)2μ-Cl]2; 2,2’-bipyridine-4,4’-dicarbonitrile In ethylene glycol at 150℃; for 45h; Inert atmosphere; Stage #2: ammonium hexafluorophosphate Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethylene glycol at 150℃; for 45h; Inert atmosphere; | 2-1 2-1: Synthesis of [Ir(btp)2(bpy-CN)2]PF5 (IrCN ) A mixture of Ir-dimer complex (0.088 g, 0.068mmol) and 4,4’-dicyano-2,2’-bipyridine (bpy-CN: 0.029 g, 0.14 mmol) in ethylene glycol (5.9 mL) was heated at 1500 C. for 45 h under nitrogen. The reaction mixture was poured into water (40 mL) and washed with diethyl ether (40 mLx2). To the aqueous layer was added ammonium hexafluorophosphate (0.610 g, 3.74 mmol). The organic mixture products were extracted with dichloromethane (40 mLx2) and the solvent was removed by rotary evaporation under vacuum. The solids were collected by filtration, washed with water and vacuum dried. The obtained crude product was purified by column chromatography on silica gel (solvent: methanol/dichloromethane, 1:6 v/v), followed by recrystallization from dichloromethane through n-hexane vapor diffusion to yield complex Ir-CN as dark-green crystals (0.056 g, 0.058 mmol, 85% yield). ‘H NMR (300 MHz, DMSO-d5) ö 9.54 (s, 2H),8.13 (d, J=7.2 Hz, 2H), 8.xx8.Ox (m, 4H), 7.95 (m, 4H), 7.77 (d, J=5.7 Hz, 2H), 7.23 (t, J=7.5 Hz, 2H), 7.08 (t, J=6.9 Hz, 2H), 6.88 (t, J=8.0 Hz, 2H), 5.86 (d, J=8.1 Hz, 2H). ‘3C NMR (100.6 MHz, DMSO-d5) ö 163.17, 155. 69, 151.87, 150.89, 145.64, 144.61, 142.10, 140.69, 136.47,132.10, 128.63, 125.84, 124.49, 124.15, 123.57, 122.67,122.21, 119.99, 115.65. ESI-MS calcd. for C44H35F5IrN5PS2, 819.0977 [M-PF5 found 819 [M-P F5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In chloroform at 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | Stage #1: [Ru(1,10-phenanthroline)2Cl2]; 2,2’-bipyridine-4,4’-dicarbonitrile With water In ethanol for 18h; Reflux; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; lithium chloride In ethylene glycol at 180℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | Stage #1: [Ru(1,10-phenanthroline)2Cl2]; 2,2’-bipyridine-4,4’-dicarbonitrile With water In ethanol for 18h; Inert atmosphere; Reflux; Stage #2: ammonium hexafluorophosphate With water | (2,2'-bipyridine-4,4'-carboxamide)bis(1,10-phenanthroline)ruthenium(II) hexafluorophosphate [Ru(CONH2-bpy)(phen)2](PF6)2 (4) (Comparative) RuCl2(phen)2 (150 mg, 0.28 mmol, 1.0 equiv.) and 2,2'-Bipyridine-4,4'-dicarbonitrile (64 mg, 0.31 mmol, 1.1 equiv.) were dissolved in a 1:1 mixture of H2O/EtOH (30 mL) and were refluxed for 18 h under N2 atmosphere. The solvent was evaporated and the residue redissolved in 5 mL of H2O. A saturated, aq. NH4PF6 solution was added and the resulting precipitate was collected by vacuum filtration. The solid was washed with H2O (50 mL) and Et2O (50 mL). The product was purified by column chromatography on silica gel with an CH3CN /aq. KNO3 (0.4 M) solution (10:1). The fractions containing the product were united and the solvent was removed. The residue was dissolved in CH3CN and undissolved KNO3 was removed by filtration. The solvent was removed again and the product was dissolved in H2O (50 mL). Upon addition of NH4PF6 the product precipitated as a PF6 salt. The solid was obtained by filtration and was washed with H2O (50 mL) and Et2O (50 mL). The product was dried in high vacuum. Yield: 16%. 1H NMR (400 MHz, CD3CN) δ = 8.97 (2H, s), 8.67 (2H, d, 3J = 8.3 Hz), 8.58 (2H, d, 3J = 8.3 Hz), 8.30-8.22 (4H, m), 8.18 (2H, d, 3J = 5.2 Hz), 7.87-7.84 (4H, m), 7.79 (2H, dd, 3J = 8.3 Hz, 3J = 5.2 Hz), 7.61-.7.57 (4H, m), 7.25 (2H, s), 6.48 (2H, s). 13C NMR (100 MHz, CD3CN) δ = 165.7, 158.8, 154.0, 153.9, 153.5, 148.6, 148.3, 143.0, 138.2, 138.0, 132.1, 132.0, 129.1, 129.0, 127.0, 127.0, 126.0, 123.1. HR-MS (ESI + m/z): Calcd. [M-2PF 6] 2+ : 352.06056; found: 352.06063. EA (%): Calcd. for (C36H26F12N8O2P2Ru): C 43.52, H 2.64, N 11.28; found. C 43.33, H 2.47, N 11.15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In toluene for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 3 h / Reflux 2: acetone / 4 h / Reflux; Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: [bis[2-(benzo[b]thiophen-2-yl)quinoline]iridium(III)(μ-Cl)]2; 2,2’-bipyridine-4,4’-dicarbonitrile In methanol; dichloromethane at 70℃; for 24h; Inert atmosphere; Stage #2: potassium hexafluorophosphate In methanol; dichloromethane at 20℃; for 2h; | 1 Weigh 101.6 mg of the ligand with the structure shown in formula III and 43.3 mg of 4,4'-dicyano-2,2'-bipyridine, dissolve them in a mixed solvent of 30mL CH3OH and 30mL CH2Cl2, and condense and reflux at 70°C under nitrogen protection React for 24 hours, add 0.8 mmol potassium hexafluorophosphate to the resulting chloride ion-containing iridium complex system, stir at room temperature for 2 hours, collect the filtrate by suction under reduced pressure, and carry out column chromatography separation to obtain the structure of formula I containing dicyanide Base iridium complex [(btpq)2-Ir-bpy-2CN)][PF6]. |
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