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CAS No. : | 148332-36-9 | MDL No. : | MFCD04114290 |
Formula : | C16H11N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZYTWXMBGOUJDHJ-UHFFFAOYSA-N |
M.W : | 277.28 | Pubchem ID : | 2762749 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 77.66 |
TPSA : | 75.97 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.93 cm/s |
Log Po/w (iLOGP) : | 2.19 |
Log Po/w (XLOGP3) : | 1.49 |
Log Po/w (WLOGP) : | 2.9 |
Log Po/w (MLOGP) : | -0.37 |
Log Po/w (SILICOS-IT) : | 2.83 |
Consensus Log Po/w : | 1.81 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.93 |
Solubility : | 0.323 mg/ml ; 0.00116 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.69 |
Solubility : | 0.563 mg/ml ; 0.00203 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.69 |
Solubility : | 0.000571 mg/ml ; 0.00000206 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.55 |
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 |
---|---|---|
89% | With thionyl chloride; at 60℃; for 16h; | Compound 8 (5.05 g, 18.2 mmol) was dispersed in 200 ml of dry methanol and cooled to 0°C. Thionyl chloride (7.93 ml, 13.0 g, 109 mmol) was added dropwise. After complete addition the mixture was heated for 60°C and stirred for 16 h. The solvent was removed under reduced pressure and 80 mlof saturated aqueous NaHCO3 solution was added. The mixture wasextracted with DCM (3x50 ml). The combined organic phases weredried over Na2SO4 and the solvent was removed underreduced pressure. The product was obtained as a white solid. Yield: 4.74 g(89percent) mp:208-209°C.1H-NMR(500 MHz, DMSO-d6): delta 8.86 (s, 2H), 8.76 (ddd, J = 4.7 Hz, 1.7 Hz, 0.9 Hz, 2H), 6.64 (dt, J = 7.9 Hz, 0.9 Hz, 2H), 8.04 (td, J = 7.8 Hz, 1.8 Hz, 2H), 7.54 (ddd, J = 7.5 Hz, 4.7 Hz, 1.1 Hz, 2H), 3.98 (s, 3H) 13C-NMR (126 MHz, DMSO-d6): delta165.0, 156.1, 154.0, 149.5, 139.3, 137.6, 124.9, 120.9, 119.3, 52.9HRMS (ESI, m/z): calcd for C17H14N3O2 [M+H]+: 292.1081; Found: 292.1079. |
General procedure: Typically, 2-(4-carboxyphenyl)-4,6-dipyrid-2-yltriazine (1.0 g,2.81 mmol) was heated to reflux in thionyl chloride (30 mL) for0.5 h, after which no solid suspension remained. The excess thionylchloride was removed by distillation and the residue was driedunder vacuum, dry methanol (60 mL) was added and the reactionmixture was heated to reflux until no solid suspension remained(2 h). The solution was cooled to room temperature and addedto H2O (300 mL) forming a voluminous precipitate of the methylester ligand which was isolated by filtration and dried in vacuowithout further purification. Typically, the ligand (0.25 g,0.68 mmol) was heated to reflux in DMF with RuCl3 (0.07 g,0.34 mmol) and AgNO3 (0.173 g, 1.02 mmol) after which the solutionwas filtered to remove AgCl(s). The filtrate was then decantedinto a solution of NH4PF6 (aq) (300 mL), and the resultant heavyprecipitate was isolated by filtration and washed with water, thendissolved in a minimal amount of acetonitrile for chromatographicpurification using silica and a 7:2 CH3CN/KNO3 (aq, sat) mixture aseluent. The collected fractions are combined, and to this addedNH4PF6 and enough DCM to effect a phase separation. After washingthe organic phase, the aqueous phase was discarded and theprocess repeated, with a final washing with water alone. Theorganic phase was dried and the residue taken up in a minimalamount of acetonitrile, then poured into H2O (300 mL) to give aheavy precipitate which was filtered and dried in vacuo. Yield:0.263 g (69percent), Rf = 0.55 (silica, 7:2 CH3CN/KNO3 (sat, aq) as eluent).1H NMR (400 MHz, CD3CN) d ppm 9.19 (d, J = 8.4 Hz, 4H), 9.14 (d,J = 7.7 Hz, 4H), 8.44 (d, J = 8.4 Hz, 4H), 8.16 (m, 4H), 7.73 (d,J = 5.3 Hz, 4H), 7.41 (m, 4H), 4.02 (s, 3H). ESI-MS: [M]2+ Cald. forC42H30N10O4Ru: 420.07475. Found: 420.07499. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water; at 120 - 180℃; | 1.0 mmol of CuSO4 and 0.5 mmol of 2,2 ':6',2"-terpyridine-4'-carboxylic acid were mixed, and placed in a stainless steel-lined stainless steel reactor. 20 mL of deionized water and 10 mL of absolute ethanol were added, mixed evenly, sealed, and hydrothermal reaction was carried out at 120-180 ° C for 3 ~ 5 days under high temperature and high pressure environment to increase the reaction. The oxidation-reduction potential of the material changes significantly to improve the reaction rate. After completion of the hydrothermal reaction, the stainless steel reactor was cooled to room temperature by 5 ° C per hour to obtain a blue block of 2,2 ': 6', 2 'tripyridine-4'-carboxylic acid copper sulfate crystals. The resulting crystals were ground to 100 mesh sieve, to obtain terpyridine-4 '-carboxylic acid copper hydrogensulfate monoclinic blue powder having purity of not less than 99percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere; | (Step 1)To a solution of 2,2?:6?,2?-terpyridine-4?-carboxylic acid (200 mg, 0.72 mmol) in DMF (3.6 mE) were added potassium carbonate (20 mg, 1.4 mmol) and methyl iodide (0.07mE, 1.1 mmol), and the reaction mixture was stirred at room temperature for 16 hr. To the reaction mixture was added brine, and the aqueous layer was extracted with ethyl acetate (3x5.0 mE), and the extract was washed with brine, anddried over magnesium sulfate. The mixture was filtered, and concentrated under reduced pressure to give a crude product.The obtained crude product was used for the next reaction without purification. To a solution of the crude product (0.72 mmol) in tetrahydrofuran (7.2 mE) was added lithium alu15 minum hydride (28 mg, 0.7 mmol) at 00 C. After stirring for3 hr, sodium sulfate 10 hydrate was added to the reactionmixture, and the mixture was stirred at room temperature for1 hr. The reaction mixture was filtered through a celite pad,and the filtrate was concentrated under reduced pressure. The residue was dissolved in pyridine (3.6 mE), and acetic anhydride (0.14 mE, 1.4 mmol) was added to the solution. Afier stirring for 16 hr, toluene was added to the mixture, and concentrated under reduced pressure. The residue waspurified by CHROMATOREX Diol silica gel column chromatography (eluent: n-hexane:ethyl acetate=1:0-1 :1) to give 2,2?:6?,2?-terpyridine-4?-ylmethyl acetate (88 mg, yield 40%3 steps) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid; In water; N,N-dimethyl-formamide; acetonitrile; at 120℃; for 72h; | Take the material according to the following specific mass or volume:Htpc (27.7 mg, 0.1 mmol),CrCl3·6H2O (40 mg, 0.15 mmol),DMF (12.9 mmol, 1 mL),CH3CN (1mL),H2O (9mL),HNO3 (21 uL, 7 mol/L).The above materials were placed in a 25 mL reaction kettle.Stir for 0.5 to 1.5 hours,Warming up to 120 ° C,After 3 days of reaction,Naturally cooled to room temperature,Light red crystals were observed,Is the target product,Filter it out of the mother liquor,Water washing,It is naturally dry after finishing. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 3h; | Synthesized according to the route shown in Figure 4.TpyCOOH (0.55 g, 2 mmol) was added to the dried flask,Aminothiazole compound Tz-NH2 (0.47 g, 2 mmol),Dicyclohexylcarbodiimide DCC (0.41 g, 2 mmol),30 mL of N,N-dimethylformamide was stirred at room temperature for 3 hours.The solvent was evaporated under reduced pressure, washed with water and dried in vacuo.That is, the ligand tpyL1.The yield was 0.94 g and the yield was 95percent.Precursor complex [Ru(tpy)Cl3] (0.79 g, 1.8 mmol) and ligand tpyL1 (0.94)g, 1.9 mmol) in the flask,50 mL of ethylene glycol methyl ether and 0.5 mL of 4-ethylmorpholine were added and refluxed for 4 hours.Cool to room temperature, filter,To the filtrate was added saturated KPF6 (815 mg, 5 mmol) to precipitate a precipitate.Filtration was carried out to collect a precipitate, which was washed with water and diethyl ether, and then dried in vacuo to give a crude product.The single red component was eluted by silica gel column chromatography in a mixed solvent of acetonitrile and methanol (volume ratio: 4:1) to obtain the target terpyridine pyridinium (II) complex RuTz1.The output is 1.48 g,The yield was 74percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.99 g | With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 3h; | Synthesized according to the route shown in Figure 6.Taking tert-butoxycarbonylglycine (0.35 g, 2 mmol) and aminothiazole compoundTz-NH2 (0.47 g, 2 mmol),Dicyclohexylcarbodiimide DCC (0.41 g, 2 mmol),30 mL of N,N-dimethylformamide was stirred at room temperature for 3 hours.The solvent was evaporated under reduced pressure to give a white solid. The solid was dissolved in 20 mL of dichloromethane and then added with trifluoroAcetic acid (1.03 g, 9 mmol) was stirred for 1 hr. Add N,N-dimethylformamide30 mL dissolved, added tpyCOOH (0.55 g, 2 mmol), dicyclohexylcarbodiimide DCC (0.41 g, 2 mmol), 30It was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, washed with water and dried in vacuo to give a white solid. Production volume 0.99g, yield 90percent. Precursor complex [Ru(tpy)Cl3] (0.79 g, 1.7 mmol) and ligand tpyL3 (0.99 g, 1.8)Methyl) 50 mL of ethylene glycol methyl ether and 0.5 mL of 4-ethylmorpholine were added to the flask and refluxed for 4 hours. Cool to room temperature, filter,To the filtrate was added saturated KPF6 (815 mg, 5 mmol), and the precipitate was precipitated.It was then vacuum dried to give a crude product. Chromatography on silica gel column, eluting with a mixture of acetonitrile and methanol (volume ratio 2:1)The color component gives the target terpyridine pyridinium (II) complex RuTz3. The yield was 1.43 g and the yield was 72percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydroxide In water at 160℃; for 96h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: (2,2':6',2''-terpyridine)trichlororuthenium(III); [2,2′:6′,2′′-terpyridine]-4′-carboxylic acid With N-ethylmorpholine; In ethanol; water for 4h; Reflux; Inert atmosphere; Stage #2: ammonium hexafluorophosphate In water | [Ru(terpy)(terpy COOH)](PF6)2 (5) The synthesis of [Ru(terpy)(terpy-COOH)](PF6)2 was previouslyreported [45]. In this work, another synthetic route was employed. Ru(terpy)Cl3 (200 mg, 0.45 mmol, 1.0 equiv.), 4′-Carboxy-2,2′:6′,2″-terpyridine(terpy-COOH) (139 mg, 0.50 mmol, 1.1 equiv) and some dropsof N-ethylmorpholine were dissolved in 8:2 EtOH/H2O (50 mL). Themixture was heated under nitrogen atmosphere at reflux for 4 h. Aftercooling down to room temperature, the crude product was filtered overCelite and washed thoroughly with EtOH. The solvent was removed andthe solid residue dissolved in H2O. A sat. aqueous solution of NH4PF6was added and the crude product precipitated as a PF6 salt. The solidwas collected by centrifugation and washed with Ethanol, Water andEt2O. The product was isolated via fractionated precipitation fromAcetonitrile by adding dropwise Et2O. The yielded solid was isolated byfiltration and washed with pentane. Experimental data fits with theliterature. Purity of the sample was assessed by HPLC and elementalanalysis. Anal. Calc. for C31H22F12N6O2P2Ru+0.1 C5H12: C 41.63, H2.57, N 9.25. Found: C 41.84, H 2.68, N 9.56. |
Tags: 148332-36-9 synthesis path| 148332-36-9 SDS| 148332-36-9 COA| 148332-36-9 purity| 148332-36-9 application| 148332-36-9 NMR| 148332-36-9 COA| 148332-36-9 structure
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