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CAS No. : | 16858-01-8 | MDL No. : | MFCD14708176 |
Formula : | C18H18N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VGUWFGWZSVLROP-UHFFFAOYSA-N |
M.W : | 290.36 | Pubchem ID : | 379259 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 86.28 |
TPSA : | 41.91 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.91 cm/s |
Log Po/w (iLOGP) : | 2.52 |
Log Po/w (XLOGP3) : | 1.64 |
Log Po/w (WLOGP) : | 2.62 |
Log Po/w (MLOGP) : | 1.04 |
Log Po/w (SILICOS-IT) : | 3.16 |
Consensus Log Po/w : | 2.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.88 |
Solubility : | 0.38 mg/ml ; 0.00131 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.13 |
Solubility : | 2.14 mg/ml ; 0.00736 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -6.86 |
Solubility : | 0.0000403 mg/ml ; 0.000000139 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.99 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
42% | With sodium hydroxide In water at 20℃; for 48 h; Inert atmosphere | Put a rotor in a 100 mL eggplant flask, attach a three-way cock, a balloon and dry in vacuum . Under a nitrogen atmosphere, 2-chloromethylpyridine · hydrochloride (2.0 g 12.2 mmol) was added Well, it was dissolved in 20 mL of distilled water. In an ice bath, a solution prepared by dissolving NaOH (2.44 g, 61.0 mmol) in a minimum amount of distilled water was added slowly, then 2-picolylamine (0.60 g, 5.54 mmol) was added and stirred. At this time, if the solution was not uniform, a small amount of distilled water was added until it became homogeneous. The color of the solution was red. Remove from ice bath, And the mixture was stirred at room temperature for 48 hours. The color of the solution gradually turned brown, A brown oily substance insoluble in the aqueous solution precipitated. 50 mL of CH 2 Cl 2 was added to the solution, transferred to a separating funnel, and partitioned with CH 2 Cl 2 to extract an organic layer (50 mL × 3). The extracted organic layer was dehydrated with Na 2 SO 4, Concentration with an evaporator gave a brown oily substance. When the oily substance obtained was well dried under vacuum in a vacuum line, A brown semi-oily solid precipitated. Washing with a small amount of Et 2 O gave a brown solid. Recrystallization of this solid from Ligroin gave 0.68 g of pale yellow needle crystals. yield 42percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In dichloromethane; water; at 0 - 20℃; for 48h;pH 9.5; | Tris[(2-pyridyl)methyl]amine (TPMA) was prepared according to a modified protocol described by Tyeklar et al. (Tyeklar Z et al. 1993). Ten grams of 2-pycolil chloride (61 .0 mmoles) were dissolved in 25 mL of distilled water and the mixture was cooled to 0C and added of 12 mL of 5 N NaOH. The solution was added of 3.2 ml_ of 2-(aminomethyl)pyridine (30.5 mmoles) and 50 ml_ of dichloromethane. The reaction mixture was allowed to reach room temperature under vigorous stirring and the pH 9.5 was maintained by 5.0 N NaOH addition. After 48 hours the organic phase was washed three times with 20 ml_ of 2.5 N NaOH and then dried with anhydrous Na2SO4 and filtered. The organic solvent was eliminated under vacuum. The TPMA was recovered by treating the resulting waxy red-brown product three times with 25 ml_ of boiling petroleum ether. The organic phase was then desiccated under vacuum. The final product yield was 5.6 g.The product was analysed by 1 H-NMR and ESI-MS.1 H-NMR (CDCIs): delta ppm 8.53 (d, J = 4.86, 3H, Py-H6), 7.65 (t, J = 7.71 , 3H, Py- H4), 7.58 (d, J = 7.71 , 3H, Py-H3), 7.14 (t, J = 6.06, 3H, Py-H5), 3.88 (s, 6H, -CH2-). ESI-MS [m/z]: 291 .15 (M+H+)1 + and 313.14 (M+Na+)1 + [calcd for Ci8H18N4: 290.15]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In acetonitrile; at 55℃; for 0.5h; | In a 100 mL round bottomed flask was placed 2-aminomethylpyridine (2.50 g, 0.023 moles). The system was placed under nitrogen. The solid was dissolved in 20 mL of acetonitrile followed by the addition of 7 mL of triethylamine. Next the 2-bromomethylpyridine hydrobromide (5.80 g, 0.023 moles) was added. The reaction mixture was allowed to stir for 0.5 hours at 55 C., whereupon the reaction was vacuumed down to residue. The mixture was purified using a large silica column (10% methanol/methylene chloride). 1H NMR (CDCl3, ppm): 3.98 (s, 4H), 7.15 (m, 2H), 7.55 (m, 2H), 7.65 (m, 2H), 8.55 (m, 2H). Mass Spectroscopy demonstrated the molecular weight to be 291 (M+1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; for 0.166667h; | A reaction liquid which was obtained by mixing a compound A4-1 (manufactured by Tokyo Chemical Industry Co., Ltd.) and copper (II) chloride dihydrate (manufactured by Wako Pure Chemical Industries, Ltd.) at a molar ratio of 1:1 in methanol and stirring the mixture for 10 minutes was dried under reduced pressure, and thus, a copper complex Cu5-1 was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 20℃; for 0.166667h;Sonication; | General procedure: Complexes 1-3 were readily synthesized by the sonochemical method according to the following procedure. In a typical experiment for the synthesis of complexes 1-3, a 5 ml solution of HgX2 (where X is Cl, Br and I) (0.1 mmol) in methanol was positioned in a round bottom flask (50 mL) and then the round bottom flask was fixed in the bath of the ultrasonic generator operating at 40 kHz with a maximum power output of 305 W. Into this solution a 5 ml solution of the <strong>[16858-01-8]TPA</strong> ligand (0.1 mmol) in methanol was added dropwise. After the ultrasonic irradiation for 10 min, the obtained precipitate was filtered off, washed with a small amount of methanol and dried in air. The products of the three separate sonochemical reactions were characterized by different techniques such as powder X-ray diffraction (PXRD), FT-IR spectroscopy and elemental analysis. The elemental analysis and FT-IR spectra of the prepared complexes by the sonochemical method and by the conventional method are indistinguishable. The morphology and size of the prepared products by the sonochemical method were examined by Field-Emission Scanning Electron Microscopy (FE-SEM). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In methanol soln. Fe(ClO4)2*6H2O in MeOH was added to soln. tris(2-pyridylmethyl)amine in MeOH and stirred for 30 min, 3,6-dipyridin-2-yl-1,4-dihydro(1,2,4,5)tetrazine was added and refluxed for 4 h; ppt. was filtered hot, washed with Et2O and dried in air; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In ethanol; water to a hot soln. of Cu salt and amine added dropwise an aq. soln. of Na salt, heated on a steam bath for 15 min; filtered, stored at room temp. for 1 d, ppt. filtered, crystd. (water); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Embodiment 4Production of the Ligand tris-[(2-pyridyl)-methyl]amine (tmpa) 4 mL (42.0 mmol) freshly distilled pyridine-2-carbaldehyde (6) was added to a mixture of 2.16 g (20.0 mmol) 2-(aminomethyl)pyridine (9) and 12.6 g (214 mmol) sodium triacetoxyborohydride in 300 mL dichloromethane. After the yellowish mixture was stirred for 18 h at room temperature, a saturated solution of sodium hydrogen carbonate was added. The mixture was stirred 15 min at room temperature, extracted twice with ethyl acetate and the combined organic phases were dried over magnesium sulfate. The solvent was removed and the yellow, viscous remainder was extracted three times with petroleum ether. The combined organic phases were freed from the solvent in vacuum. A yellowish solid was obtained as the product (4).1H-NMR (CDCl3): 8.55 (3H, d), 7.84 (3H, t), 7.79 (3H, d), 7.24 (3H, m), 3.87 (6H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Tmpa (0.1 g 0.344 mmol) was weighed in a 50 mL eggplant flask and dissolved in 20 mL of EtOH. To this solution, When Cu (ClO 4) 2 .6H 2 0 (0.140 g 0.379 mmol) was dissolved in 10 mL and added, a light blue solid was precipitated. When this solid was allowed to stand, it became semi-oily and remained at the bottom. The supernatant was removed and repeatedly washed with EtOH to give a semi-oily blue solid. This was vacuum dried well in a vacuum line to obtain a light blue solid. This solid was dissolved in MeCN / acetone (v: v = 1: 1) and recrystallized from liquid-liquid diffusion of MeCN-acetone-Et 2 O to obtain a dark blue single crystal suitable for single crystal X-ray structural analysis. This crystal was weathered, and when it was taken out from the solution it broke down into a powder of light blue color |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In acetonitrile; at 20℃; for 5h; | General procedure: To a solution of cobalt(II) perchloratehexahydrate (0.37 g, 1 mmol) in acetonitrile (5 mL) added a solution (5 mL) of the ligand (0.29 g, 1 mmol) in acetonitrile.To the resulting solution solid sodium benzoylformate (0.17 g,1 mmol) was added and the resulting mixture was stirred for 5 h.The solution was concentrated to 1 mL and diethyl ether (10 mL) was added. The mixture was then stirred for 1 h to precipitate a green solid which was isolated by filtration, washed 2-3 times with diethyl ether, and dried. C26H23ClCoN4O7(597.87 g/mol): calcd. C 52.23, H 3.88, N 9.37; found C 52.54, H3.79, N 9.57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In methanol; at 20℃; for 5h; | General procedure: Cobalt(II) perchlorate hexahydrate (0.37 g, 1 mmol) was added toa solution of the ligand (1 mmol) in methanol (5 mL). To the resulting solution sodium benzoylformate (0.17 g, 1 mmol) in methanol (2 mL) was added. The solution was then stirred at room temperature for 5 h. A solid compound was isolated from the reaction solution upon addition of 1 mmol sodium tetraphenylborate. The compound was then filtered, washed with methanol, and dried. C50H43BCoN4O3 (817.62 g/mol): calcd. C 73.45, H5.30, N 6.85; found C 73.32, H 5.33, N 6.57. Single crystals suitable for X-ray diffraction were obtained by vapor diffusion of diethyl ether into a tetrahydrofuran-acetonitrile solution of the complex. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In methanol; at 20℃; for 5h; | To a solution of the ligand <strong>[16858-01-8]TPA</strong>(0.29 g, 1 mmol) in methanol (5 mL) was added solid cobalt(II)perchlorate hexahydrate (0.36 g, 1 mmol). The orange-red solution was then treated with solid sodium phenylpyruvate (0.18 g,1 mmol) and the resulting green solution was stirred for a further5 h at room temperature. After treating the reaction solution with NaBPh4 (1 mmol), a green solid was isolated. The solid was isolated by filtration, washed with methanol, and dried. C51H45BCoN4O3 (831.67 g/mol): calcd. C 73.65, H 5.45, N6.74; found C 73.33, H 4.97, N 6.91 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | The copper(II) salt Cu(CF3SO3)2 (112 mg, 0.31 mmol) and TMPA (100 mg, 0.34 mmol) were dissolved in acetone (25 mL) and the resulting light green solution was stirred at room temperature for 30 min. Then 4,4'-bipyridine (25 mg, 0.16 mmol) was added and the solution was left under gentle reflux for 4 h. After cooling to room temperature acetone was removed to dryness and the green blue solid was dried under low pressure, washed twice with Et2O before recrystallisation in a acetone/ethylacetate mixture. Light blue crystals suitable for X-ray analysis were obtained. Yield 40 mg (18%). Anal. Calc. for C50H45Cu2F12N10O12S4: C, 41.1; H, 3.1;N, 9.6. Found: C, 40.8; H, 3.0; N, 9.5%. FT-IR (KBr pellet): 3070w,2926w, 1609m, 1574w, 1481m, 1441m, 1409w, 1371w, 1262vs,1227m, 1160s, 1097w, 1032s, 883w, 843w, 808m, 771m, 639s,574m, 518m, 413m cm1. UV-Vis (acetone): kmax, 905 nm (e,177 cm-1 L mol-1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | A solution of Co(BF4)2H2O (102.4 mg, 0.3 mmol) in dry methanol (10 mL) was added to a solution of tris(2-pyridylmethyl)amine (87.6 mg, 0.3 mmol). The resulting solution was stirred for 1 hr, and then 30 mL of <strong>[4877-80-9]2,3,6,7,10,11-hexahydroxytriphenylene</strong> (H6L, 32.5 mg, 0.1 mmol) dissolved in methanol containing triethylamine was added dropwise. The resulting solution was stirred for 1 hr. Diethylether was added to the solution slowly to obtain the complex. This solution was cooled to -5 °C and over the period of 10 days a deep green microcrystals of [Co3(tpa)3(L)](BF4)4 separated from the solution in 69percent (119.3 mg) yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | In water; acetone; for 336h; | Synthesis: A acetone/H2O solution (5:1mL) containing <strong>[16858-01-8]TPA</strong> (0.1mmol) and CoCl2·2H2O (0.1mmol) and KPF6 (0.2mmol) was layered on a aqueous solution (5mL) of K3Fe(CN)6 (0.02mmol). After two weeks, green crystal samples were obtained (yield of 15%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | In water; acetone; for 336h; | A acetone/H2O solution (5:1 mL) containing <strong>[16858-01-8]TPA</strong> (0.1 mmol) and CoCl2*2H2O (0.1 mmol) and KPF6 (0.2 mmol) was layered on a aqueous solution (5mL) of K3Fe(CN)6 (0.02 mmol). After two weeks, green crystal samples were obtained (yield of 15%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In acetone; at 20℃; for 1h;Inert atmosphere; | General procedure: For each reaction, 0.096g (1.2×10-4mol) of [MII(NCMe)6](SbF6)2 (M=Mn, Fe, or Co) were dissolved in approximately 5mL of acetone resulting in colorless solutions for both Mn and Fe, but a pink solution for Co. Next, 0.036g (1.2×10-4mol) of TPyA dissolved in minimal amounts of acetone were quantitatively transferred to each stirring solution of [MII(NCMe)6](SbF6)2 resulting in homogenous solutions of [MII(NCMe)6](SbF6)2 and TPyA (colorless for Mn, light yellow for Fe, and violet for Co). Finally, 0.044g (1.2×10-4mol) of L partially dissolved in 20mL of acetone (yellow suspension) were transferred to stirring solutions of [MII(NCMe)6](SbF6)2 and TPyA resulting in homogeneous yellow and orange solutions for Mn and Fe, respectively; where as a heterogeneous orange solution (fine suspension) was obtained for Co. Enough acetone was added to each reaction to bring the total volumes of these solutions to approximately 50mL. The Mn reaction solution was stirred for 1h at room temperature, filtered, and taken to dryness under vacuum yielding an orange film. The Fe and Co reaction solutions were taken out of the glove box, attached to the Schlenk line, and allowed to reflux for approximately 3h with a water-cooled condenser. After refluxing, these solutions were allowed to cool, taken inside the glove box, filtered, and concentrated to dryness under vacuum both resulting in uniform orange films. All three films of the products were redissolved in minimal amounts of acetone (~3-4mL) and gravity filtered into 20mL scintillation vials. These vials were then placed inside vapor jars containing Et2O in the dry-box. After 2days, yellow crystals of 1, orange crystals of 2, and dark orange crystals of 3 suitable for single crystal X-ray analyses were formed. Yield and IR spectral data of 1-3 are summarized below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In acetone; for 3h;Inert atmosphere; Schlenk technique; Reflux; | General procedure: For each reaction, 0.096g (1.2×10-4mol) of [MII(NCMe)6](SbF6)2 (M=Mn, Fe, or Co) were dissolved in approximately 5mL of acetone resulting in colorless solutions for both Mn and Fe, but a pink solution for Co. Next, 0.036g (1.2×10-4mol) of TPyA dissolved in minimal amounts of acetone were quantitatively transferred to each stirring solution of [MII(NCMe)6](SbF6)2 resulting in homogenous solutions of [MII(NCMe)6](SbF6)2 and TPyA (colorless for Mn, light yellow for Fe, and violet for Co). Finally, 0.044g (1.2×10-4mol) of L partially dissolved in 20mL of acetone (yellow suspension) were transferred to stirring solutions of [MII(NCMe)6](SbF6)2 and TPyA resulting in homogeneous yellow and orange solutions for Mn and Fe, respectively; where as a heterogeneous orange solution (fine suspension) was obtained for Co. Enough acetone was added to each reaction to bring the total volumes of these solutions to approximately 50mL. The Mn reaction solution was stirred for 1h at room temperature, filtered, and taken to dryness under vacuum yielding an orange film. The Fe and Co reaction solutions were taken out of the glove box, attached to the Schlenk line, and allowed to reflux for approximately 3h with a water-cooled condenser. After refluxing, these solutions were allowed to cool, taken inside the glove box, filtered, and concentrated to dryness under vacuum both resulting in uniform orange films. All three films of the products were redissolved in minimal amounts of acetone (~3-4mL) and gravity filtered into 20mL scintillation vials. These vials were then placed inside vapor jars containing Et2O in the dry-box. After 2days, yellow crystals of 1, orange crystals of 2, and dark orange crystals of 3 suitable for single crystal X-ray analyses were formed. Yield and IR spectral data of 1-3 are summarized below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In acetone; for 3h;Inert atmosphere; Schlenk technique; Reflux; | General procedure: For each reaction, 0.096g (1.2×10-4mol) of [MII(NCMe)6](SbF6)2 (M=Mn, Fe, or Co) were dissolved in approximately 5mL of acetone resulting in colorless solutions for both Mn and Fe, but a pink solution for Co. Next, 0.036g (1.2×10-4mol) of TPyA dissolved in minimal amounts of acetone were quantitatively transferred to each stirring solution of [MII(NCMe)6](SbF6)2 resulting in homogenous solutions of [MII(NCMe)6](SbF6)2 and TPyA (colorless for Mn, light yellow for Fe, and violet for Co). Finally, 0.044g (1.2×10-4mol) of L partially dissolved in 20mL of acetone (yellow suspension) were transferred to stirring solutions of [MII(NCMe)6](SbF6)2 and TPyA resulting in homogeneous yellow and orange solutions for Mn and Fe, respectively; where as a heterogeneous orange solution (fine suspension) was obtained for Co. Enough acetone was added to each reaction to bring the total volumes of these solutions to approximately 50mL. The Mn reaction solution was stirred for 1h at room temperature, filtered, and taken to dryness under vacuum yielding an orange film. The Fe and Co reaction solutions were taken out of the glove box, attached to the Schlenk line, and allowed to reflux for approximately 3h with a water-cooled condenser. After refluxing, these solutions were allowed to cool, taken inside the glove box, filtered, and concentrated to dryness under vacuum both resulting in uniform orange films. All three films of the products were redissolved in minimal amounts of acetone (~3-4mL) and gravity filtered into 20mL scintillation vials. These vials were then placed inside vapor jars containing Et2O in the dry-box. After 2days, yellow crystals of 1, orange crystals of 2, and dark orange crystals of 3 suitable for single crystal X-ray analyses were formed. Yield and IR spectral data of 1-3 are summarized below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | for 0.25h;Heating; | General procedure: To a hot mixture of copper(II) perchlorate hexahydrate (0.190 g, 0.50 mmol) and di(2-pyridyl) amine (0.172 g, 1.0 mmol) dissolved in 20 mL H2O, disodium squarate was added (0.081 g, 0.50 mmol). The resulting solution was heated for 15 min, filtered through celite and allowed to crystallize at room temperature. After one week, the green crystals which separated were collected by filtration, washed with 4 mL of cold propan-2-ol then ether and air dried (overall yield: 251 mg, 87%). Crystals suitable for X-ray structure determination were obtained from dilute aqueous solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With sodium tetrahydridoborate; carbon dioxide; ammonium acetate In tetrahydrofuran at 20℃; for 18h; | |
Multi-step reaction with 2 steps 1.1: methanol / 10 h / 20 °C 1.2: 2 h 2.1: glacial acetic acid; sodium cyanotrihydridoborate / methanol / 72 h / 0 °C | ||
Multi-step reaction with 2 steps 1.1: methanol / 2 h / 20 °C 1.2: 15 h / 20 °C 2.1: potassium carbonate / acetonitrile / 144 h / Darkness; Inert atmosphere |
Multi-step reaction with 2 steps 1.1: methanol / 1 h / 20 °C 1.2: 0 - 20 °C 2.1: glacial acetic acid / methanol / 1 h / 20 °C 2.2: 0 - 20 °C | ||
91 %Chromat. | With hydrogen; ammsnium formate In ethyl acetate at 60℃; for 24h; Autoclave; | 2.4. Consecutive reductive amination General procedure: In a typical procedure for reductive amination of 1a with 3a for6a synthesis, the reaction was performed in a stainless-steel autoclave(25 mL) equipped with a Teflon-inner layer and a magneticstirrer. 1a (1.5 mmol), Rh2P/NC-1 (20 mg), 3a (0.3 mmol) and ethylacetate (3.0 mL) were continuously loaded into the reactor. H2(0.5 MPa) was purged slowly into the autoclave for three timesto replace the air inside. H2 (3.0 MPa) was then reloaded slowlyinto the reactor at room temperature, and the reaction was performedfor 24 h at 60 °C with the stirring speed of 500 rpm. Theresulting reaction mixture in the reactor was analyzed by GasChromatography after the reaction, and 6a was isolated by flashcolumn chromatography. Excess amount of 1a was used to shiftthe reaction to 6a side; therefore, conversion rate of the 1a/3ato-6a should be determined by 3a. Unfortunately, 3a concentrationcannot be quantified by GC; therefore, conversion rate of 3a wasnot provided in this research. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetramethylammonium hydroxide pentahydrate; In methanol; at 20℃; for 4h;Inert atmosphere; | Under a N2 atmosphere, a methanol solution (2 mL) of Zn(ClO4)2.6H2O (40 mg, 0.11 mM) was added to solid <strong>[16858-01-8]TPA</strong> (39 mg, 0.13 mM) and the solution was stirred until the chelate ligand had dissolved. The resulting mixture was combined with a methanol solution (2 mL) containing 3-hydroxyflavone (32 mg, 0.13 mM) and Me4NOH5H2O (24 mg, 0.13 mM). This mixture was stirred for 4 h at ambient temperature. The solvent was then removed under reduced pressure and the residual solid dissolved in CH2Cl2. The CH2Cl2 solution was filtered through a celite/glass wool plug, and the product was precipitated via the addition of excess hexanes (40 mL). The isolated solid was dried under reduced pressure. Recrystallization via Et2O diffusion into CH3CN yielded yellow crystals suitable for X-ray crystallography (74 mg, 80%). Anal. Calcd for C33H27ClN4O7Zn (%): C, 57.24; H, 3.93; N, 8.09. Found: C, 57.55; H, 4.00; N, 7.84. 1HNMR (CD3CN, 300 MHz) delta 8.9 (br, 2H), 8.80-8.45 (br, 4H), 8.03-7.77 (br, 3H) 7.76-7.59(m, 4H), 7.58-7.20 (m, 8H), 4.79-4.02 (bs, 6H) ppm; UV-vis (CH3CN), nm (epsilon, M-1 cm-1)415 (19,000), 313 (7600); FTIR (KBr, cm-1) 1558 (nuC=O), 1088 (nuClO4), 619 (nuClO4);MALDI-MS, m/z (relative intensity) C33H27N4O3Zn: Calcd: 591.1369; Found: 591.1385([M-ClO4]+, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane-d2; at -78℃;Inert atmosphere; Sealed tube; Schlenk technique; | General procedure: In a N2 filled drybox, an NMR tube was charged with [RhCl(C2H4)2]2 (10 mg, 0.0257 mmol). The tube was fitted with a screwcap with a PTFE septum and brought out of the drybox. Dry, degassed d2-CD2Cl2 (0.30 mL) was added via syringe and the resulting solution was cooled to 78 C. <strong>[16858-01-8]TPA</strong> (15 mg, 0.0516 mmol) was weighed into a 5 mL vial in the drybox. The vial was sealed with a septum and brought out of the drybox. Dry, degassed d2-CD2Cl2 (0.30 mL) was used to transfer the <strong>[16858-01-8]TPA</strong> solution into the cooled Rh-dimer solution by dropwise addition with a syringe. With a microsyringe 2,4,6-trimethoxybenzene solution or tetramethylsilaneas internal standard was added. For azarhodacyclobutanes, 2, 3, 12, and 13 the solution was allowed to warm to room temperature. One equivalent of the nitrene precursor (0.0516 mmol) was added, the tube was inverted several times and let stand at room temperature for 8 h. When carbamate-based precursors 10 and 11 were employed, pyridine (20 mL, 0.258 mmol) was added and the addition of 10/11 was performedat 78 C. After 8 h, the reaction mixture was quenched with a saturated NaHCO3 solution, separated, and the organic phase was concentrated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | To a mixture of tris(2-pyridylmethyl)amine, TPA (0.146g, 0.50mmol) and Cu(ClO4)2·6H2O (0.109g, 0.50mmol) dissolved in MeOH (20mL), <strong>[499-80-9]pyridine-2,4-dicarboxylic acid</strong> disodium salt (Na2Py2,4-dc) (0.054g, 0.25mmol) dissolved in 5.0mL H2O was added drop by drop. The resulting solution was heated for 5min on a steam-bath, filtered through Celite and then was allowed to stand at room temperature. After two days, the resulting crude solid was collected by filtration and recrystallized from H2O to produe aqua blue single crystals of X-ray quality. These were collected by filtration, washed with propan-2-ol, Et2O and dried in air (overall yield: 0.105g, 61percent based on Na2Py2,4-dc). Characterization: C50H50Cl2Cu3N10O20 (1372.58g/mol): Anal. Calc.: C, 43.75; H, 3.67; N, 10.20. Found: C, 43.42; H, 3.59; N, 10.60percent. Selected IR bands: 3567 (w, br) [nu(O?H) stretching)]; 1636 (s) [nu(CO)]; 1606 (s), 1559 (m), 1480 (m), 1443 (m), 1311 (s), 1329 (s); 1082 (vs), 1051 (m) [nu(Cl?O) (ClO4?)]. UV?Vis (CH3CN): lambdamax, nm (epsilonmaxM?1cm?1 per Cu atom): ?660 (72), 870 (148, br). Molar conductivity, LambdaM in CH3CN=269Omega?1cm2mol?1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With lithium hydroxide; In methanol; for 0.0833333h; | To a mixture of <strong>[16858-01-8]tris(2-pyridylmethyl)amine</strong>, <strong>[16858-01-8]TPA</strong> (0.146g, 0.50mmol) and Cu(ClO4)2·6H2O (0.109g, 0.50mmol) dissolved in MeOH (20mL), 2,3-pyrazine-dicarboxylic acid (H2Pyaz2,3-dc) (0.054g, 0.25mmol) which was neutralized with LiOH (0.012g, 0.5mmol) dissolved in 5.0mL H2O was added drop by drop. The resulting solution was heated for 5min on a steam-bath, filtered through Celite and then was allowed to stand at room temperature. The resulting precipitate, which was obtained after four days was collected by filtration and recrystallized from H2O to produe aqua blue single crystals of X-ray quality. These were collected by filtration, washed with propan-2-ol, Et2O and dried in air. (overall yield: 62mg, 25% based on H2Pyaz2,3-dc) Characterization: C84H88Cl6Cu5N18O38 (2516.19g/mol) Anal. Calc.: C, 40.10, H, 3.53, N, 11.13. Found: C, 40.18; H, 3.46; N, 11.22%. Selected IR bands: ?3550 (w, br) [nu(O-H) stretching)]; 1607 (s) [nu(CO)]; 1572 (w), 1464 (m), 1435 (s), 1370 (w), 1309 (w); 1073 (vs), 1050 (s) [nu(Cl-O) (ClO4-)]. UV-Vis (CH3CN): lambdamax, nm (epsilonmaxM-1cm-1 per Cu atom): ?840 (193), 967 (265). LambdaM in (CH3CN)=602Omega-1cm2mol-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | General procedure: To a mixture of tris(2-pyridylmethyl)amine, TPA (0.146g, 0.50mmol) and Cu(ClO4)2·6H2O (0.109g, 0.50mmol) dissolved in MeOH (20mL), pyridine-2,4-dicarboxylic acid disodium salt (Na2Py2,4-dc) (0.054g, 0.25mmol) dissolved in 5.0mL H2O was added drop by drop. The resulting solution was heated for 5min on a steam-bath, filtered through Celite and then was allowed to stand at room temperature. After two days, the resulting crude solid was collected by filtration and recrystallized from H2O to produe aqua blue single crystals of X-ray quality. These were collected by filtration, washed with propan-2-ol, Et2O and dried in air (overall yield: 0.105g, 61% based on Na2Py2,4-dc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; at 40℃; for 0.166667h; | To a solution of HgBr2 (0.036 g, 0.1 mmol) in 5 mL methanol, a solution of the <strong>[16858-01-8]TPA</strong> ligand (0.029 g, 0.1 mmol) in 5 mL of methanol was added with stirring. The mixture was heated at 40 C for about 10 min. Reduction of the solvent volume resulted in the formation of a white precipitate. The precipitate was filtered, washed with methanol (3 × 2 mL) and dried in vacuo. The solid was then dissolved by boiling in acetonitrile (10 mL) and filtered. Upon slow evaporation of the filtrate at room temperature, crystals of complex 2 for X-ray analysis were obtained after 7 days (yield: 75%). M.p.: 164-166 C. Anal. calc. for C36H36Br6Hg3N8: C, 26.02; H, 2.18; N, 6.74. Found: C, 25.85; H, 2.12; N, 6.76%. IR (KBr pellet, cm-1): 3006 w, 2906 w, pyridine C-H; 1592 s, 1571 w, py C=N; 1475 m, 1427 s, pyridine C=C; 1370 m, 1300 m, 1257 m, 1150 m, 1094 m, 1047 m, 1007 m, 995 w, 896 w, 835 m, 765 s, 635 w, 501 w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; at 40℃; for 0.166667h; | To a solution of HgI2 (0.045 g, 0.1 mmol) in 5 mL methanol, a solution of the <strong>[16858-01-8]TPA</strong> ligand (0.029 g, 0.1 mmol) in 5 mL of methanol was added with stirring. The mixture was heated at 40 C for about 10 min. Reduction of the solvent volume resulted in the formation of a white precipitate. The precipitate was filtered, washed with methanol (3 × 2 mL) and dried in vacuo. The solid was then dissolved by boiling in acetonitrile (10 mL) and filtered. Upon slow evaporation of the filtrate at room temperature, crystals of complex 3 for X-ray analysis were obtained after 10 days (yield: 75%). M.p.: 179-181 C. Anal. calc. for C36H36I6Hg3N8: C, 22.24; H, 1.87; N, 5.76. Found: C, 22.18; H, 1.90; N, 5.78%. IR (KBr pellet, cm-1): 3007 w, 2912 w, pyridine C-H; 1593 s, 1571 w, py C = N; 1476 m, 1428 s, pyridine C=C; 1370 m, 1299 m, 1255 m, 1152 m, 1094 m, 1049 m, 1007 m, 995 w, 894 w, 835 m, 769 s, 636 w, 501 w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydroxide; In water; at 20℃; for 48h;Inert atmosphere; | Put a rotor in a 100 mL eggplant flask, attach a three-way cock, a balloon and dry in vacuum . Under a nitrogen atmosphere, 2-chloromethylpyridine · hydrochloride (2.0 g 12.2 mmol) was added Well, it was dissolved in 20 mL of distilled water. In an ice bath, a solution prepared by dissolving NaOH (2.44 g, 61.0 mmol) in a minimum amount of distilled water was added slowly, then 2-picolylamine (0.60 g, 5.54 mmol) was added and stirred. At this time, if the solution was not uniform, a small amount of distilled water was added until it became homogeneous. The color of the solution was red. Remove from ice bath, And the mixture was stirred at room temperature for 48 hours. The color of the solution gradually turned brown, A brown oily substance insoluble in the aqueous solution precipitated. 50 mL of CH 2 Cl 2 was added to the solution, transferred to a separating funnel, and partitioned with CH 2 Cl 2 to extract an organic layer (50 mL × 3). The extracted organic layer was dehydrated with Na 2 SO 4, Concentration with an evaporator gave a brown oily substance. When the oily substance obtained was well dried under vacuum in a vacuum line, A brown semi-oily solid precipitated. Washing with a small amount of Et 2 O gave a brown solid. Recrystallization of this solid from Ligroin gave 0.68 g of pale yellow needle crystals. yield 42% |
With potassium carbonate; In acetonitrile; at 80℃; for 72h; | The TPMA synthesis method comprises the steps of: adding 2-methylaminopyridine, 2-chloromethylpyridine hydrochloride, potassium carbonate and acetonitrile to a round bottom flask, and heating and refluxing at 80 C for three days.After passing through the column, a yellow-brown solid is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 0.5h; | Dichloromethane (4 mL) was added to a round bottom flask containing CuCl2 (0.10 g, 0.74 mmol) and tmpa (0.22 g, 0.74 mmol). The reaction mixture was stirred at room temperature for 30 min and product precipitated by the slow addition of pentane. Green powder was then filtered, washed with pentane and dried under vacuum. Elemental analysis: found: C, 48.0%; H, 4.7%; N, 12.3%; C18H18Cl2CuN4 requires: C, 50.9%; H, 4.3%; N, 13.2%. Crystals suitable for X-ray analysis were obtained by slow diffusion of diethylether into an acetonitrile solution of the copper(II) complex at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | A solution of Mn(O2CMe)24H2O (64.0 mg; 0.262 mmol) dissolvedin 15 mL of methanol was added to a solution of TPyA(100 mg, 0.344 mmol) dissolved in 7 mL of methanol in a 100 mLround bottom flask. To the resulting pale-pink solution was addedof chloranilic acid (36.0 mg; 0.172 mmol) dissolved in 10 mL ofmethanol resulting in a dark purple solution and formation of adark precipitate. To the mixture was added 0.05 mL (0.344 mmol)triethylamine and was then refluxed for 30 min. After filtrationwhile hot, the dark purple solution was allowed to stand for 3 daysupon which dark red crystals formed. The crystals were collectedand washed with 5 mL of methanol and allowed to dry in air(Yield: 79 mg, 38%). Key IR (cm-1; KBr): 1604 m, 1557 s, 1494 s,1434 m, 1377 m, 1356 m, 1017 m, 992 m, 865 m, 840 m, 765 m,578 m. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | The complexes were synthesized by following a common procedure.For iron(II) complex [Fe(L1)(cur)]Cl (1), a solution of ligand L1 (0.87 g,3 mmol) in 2 mL MeOH was added drop-wise to a solution of anhydrousFeCl2 (0.38 g, 3 mmol) in 3 mL MeOH. The resulting solution wasstirred at 25 C under N2 atmosphere for 1 h. A slow evaporation of thesolvent gave a dark brown solid which was washed with hexane. Thesolid (0.83 g, 2 mmol) was dissolved in 3 mL MeOH and a solution ofcurcumin (Hcur, 0.73 g, 2 mmol) in 5 mL CH2Cl2:MeOH (1:1 v/v),previously deprotonated by NEt3 (0.2 g, 2 mmol), was added drop-wiseto this with stirring at 25 C under N2 for 3 h. Solvent was evaporatedfrom the resulting dark red solution by slow evaporation and a darkbrown solid was isolated, washed with diethyl ether and cold MeOHand finally dried in vacuo over P2O5 to obtain complex 1 in analyticallypure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Under N2 conditions, a methanol solution (2 mL) of Zn(ClO4)2*6H2O (0.2 mmol) was added to L( 0.2 mmol), and the mixture was stirred until the chelating ligand had dissolved. In dark conditions, the solution was added to a methanol solution of flavonol (0.2 mmol) and Me4NOH*5H2O (0.2 mmol). The resulting mixture was stirred for 10 h at room temperature. The solvent was removed under reduced pressure and the rest of the solid dissolved in CH2Cl2. The solution was then filtered through a Celite/glass wool plug and the end product was precipitated by the addition of ethyl ether. The product was dried under reduced pressure. Yield: 83 %. dH (DMSO-d6, 400 MHz) 8.82 (d, 2H), 8.48 (d,3H), 7.94 (t, 3H), 7.87 (d, 1H), 7.79 (d, 1H), 7.70 (t, 1H), 7.52 (d,3H), 7.44 (t, 3H), 7.30 (t, 1H), 7.25 (d, 2H), 4.55 (s, 6H), 3.90 (s,3H). dC (DMSO-d6, 400 MHz) 177.15, 159.74, 154.31, 153.71,148.17, 147.04, 146.22, 140.00, 132.62, 128.84, 126.31, 124.73,124.16, 119.46, 118.43, 114.21, 55.46, 55.02. nmax (KBr)/cm11560 (nC=O), 1085 (nClO4), 619 (nClO4). lmax (CH3CN)/nm(e/M1 cm1) 423 (4510). m/z 621.1492; calcd for [(<strong>[16858-01-8]TPA</strong>)Zn(4-MeOFLH)]621.1480. Anal. Calc. for C34H29ClN4O8Zn: C65.55, H 4.69, N 8.99. Found: C 65.46, H 4.57, N 8.86 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Under N2 conditions, a methanol solution (2 mL) of Zn(ClO4)2*6H2O (0.2 mmol) was added to L( 0.2 mmol), and the mixture was stirred until the chelating ligand had dissolved. In dark conditions, the solution was added to a methanol solution of flavonol (0.2 mmol) and Me4NOH*5H2O (0.2 mmol). The resulting mixture was stirred for 10 h at room temperature. The solvent was removed under reduced pressure and the rest of the solid dissolved in CH2Cl2. The solution was then filtered through a Celite/glass wool plug and the end product was precipitated by the addition of ethyl ether. The product was dried under reduced pressure. Yield: 83 %. dH (DMSO-d6, 400 MHz) 8.90 (d, 2H), 8.76 (d,1H), 8.49 (t, 2H), 8.02 (d, 2H), 7.93 (m, 2H), 7.86 (t, 2H), 7.73 (t,2H), 7.45 (d, 2H), 7.38 (t, 2H), 7.20 (d, 2H), 7.04 (d, 1H), 4.56 (s,2H), 4.30 (s, 4H), 3.89 (s, 3H). dC (DMSO-d6, 400 MHz) 177.15,159.74, 154.31, 153.71, 148.17, 147.04, 146.22, 140.00, 132.62,128.84, 126.31, 124.73, 124.16, 119.46, 118.43, 114.21, 55.46,55.02. nmax (KBr)/cm1 1474 (nC=S), 1085 (nClO4), 619 (nClO4).lmax (CH3CN)/nm (e /M1 cm1) 500 (9430). m/z 637.1241;calcd for [(<strong>[16858-01-8]TPA</strong>)Zn(4-MeOFLTH)]637.1252. Anal. Calc. forC34H29ClN4O7SZn: C 63.90, H 4.57, N 8.77. Found: C 63.85, H4.64, N 8.83 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | The TPA ligand (0.087g, 0.3mmol) was dissolved in 5mL dry methanol under nitrogen atmosphere. To the solution, a methanolic solution of iron(II) perchlorate hydrate (0.107g, 0.3mmol) was added and was stirred for 5min followed by dropwise addition of a methanolic solution of sodium diclofenac (0.096g, 0.3mmol). A deep yellow solution was formed immediately. The reaction mixture was stirred at room temperature for 4h. The solution was then filtered to get a clear yellow filtrate. The filtrate was concentrated and diethyl ether was added dropwise to get a yellow precipitate. The yellow solid was isolated by filtration, washed with diethyl ether and dried under vacuum. Yield: 0.173g (78%). Elemental analysis calcd (%) for C32H28FeN5O6Cl3 (740.80g/mol): C, 51.88; H, 3.81; N, 9.45. Found: C, 52.29; H, 3.61; N, 9.28%. IR (KBr, cm-1): 3438(br), 3070 (br), 2923(m), 1604(s), 1506(m), 1479(m), 1448(m), 1375(m), 1307(m), 1155(m), 1093(vs), 765(m), 622(m). UV-vis in CH3CN: 258nm (epsilon=9400M-1cm-1), ESI-MS (positive ion mode in CH3CN): m/z=639.93 ([(TPA)Fe(DCF)]+, 70%). Magnetic moment: 4.52 BM. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: The TPA ligand (0.087g, 0.3mmol) was dissolved in 5mL dry methanol under nitrogen atmosphere. To the solution, a methanolic solution of iron(II) perchlorate hydrate (0.107g, 0.3mmol) was added and was stirred for 5min followed by dropwise addition of a methanolic solution of sodium diclofenac (0.096g, 0.3mmol). A deep yellow solution was formed immediately. The reaction mixture was stirred at room temperature for 4h. The solution was then filtered to get a clear yellow filtrate. The filtrate was concentrated and diethyl ether was added dropwise to get a yellow precipitate. The yellow solid was isolated by filtration, washed with diethyl ether and dried under vacuum. Yield: 0.173g (78%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: The TPA ligand (0.087g, 0.3mmol) was dissolved in 5mL dry methanol under nitrogen atmosphere. To the solution, a methanolic solution of iron(II) perchlorate hydrate (0.107g, 0.3mmol) was added and was stirred for 5min followed by dropwise addition of a methanolic solution of sodium diclofenac (0.096g, 0.3mmol). A deep yellow solution was formed immediately. The reaction mixture was stirred at room temperature for 4h. The solution was then filtered to get a clear yellow filtrate. The filtrate was concentrated and diethyl ether was added dropwise to get a yellow precipitate. The yellow solid was isolated by filtration, washed with diethyl ether and dried under vacuum. Yield: 0.173g (78%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid; at 160℃; for 72h;pH 2.52;Sealed tube; | The synthesis method of [Co2(TPMA)2(beta-Mo8O26)] is:0.1 mmol of cobalt nitrate hexahydrate, 0.1 mmol of TPMA,0.1 mmol of 1,3-ttb, 0.1 mmol of ammonium molybdate and 10 mL of water were placed in a high-pressure stainless steel reactor lined with polytetrafluoroethylene, and the pH was adjusted to 2.52 with a nitric acid solution.After sealing, the reaction kettle was placed in an oven, reacted at 160 C for 3 days, and the program was cooled.Get the wine red block crystal, that is. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 110℃; for 120h; | The synthesis method of MoO3 (TPMA) is:0.1 mmol TPMA, 0.1 mmol ammonium molybdate, 0.45 mmol hydrochloric acid,30 mL of water was mixed and placed in a container, and evaporated to reflux at 110 C for 5 days.After cooling and filtering, a yellow-brown turbid solution was obtained, and after filtration, a pale yellow clear solution was obtained, and the solution was placed in a beaker and allowed to volatilize to obtain a pale yellow rectangular crystal.That's it. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | A solution of Co(BF4)26H2O (0.10 mmol) in dry methanol(2 mL), Ar gas aerated for 5 min, was added to a stirred solutionof <strong>[16858-01-8]tpa</strong> (0.10 mmol) in dry MeOH solution (5 mL) and the resultingsolution was stirred for 30 min. A solution of Et3N (0.20 mmol) andH4L1 (0.050 mmol) in Et2O (7 mL), Ar gas aerated for 15 min, wasadded to the above methanol solution slowly. The solution wasallowed to stand at 13 C for 3 days to obtain the desired complexas a dark green precipitate. The yield obtained was 47%. IR (KBr,cm1): 3420s, 3073m, 2955m, 2120w, 1635m, 1610s, 1572m,1545w, 1482m, 1438m, 1415s, 1384m, 1349m, 1279m, 1249m,1158m, 1083s, 1056s, 1037s, 992w, 905w, 885w, 836w, 811w,771m, 730w, 699w, 667w, 642w, 612w, 582w, 532w, 522w,504w; ESI-MS, [Co2(L1)(<strong>[16858-01-8]tpa</strong>)2]2+ m/z: 536.1614; Anal. Calc. forC60H58N8O4Co2B2F86H2O: C, 53.20; H, 5.21; N, 8.27%. Found: C,52.56; H, 4.82; N, 7.51%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | General procedure: A solution of Co(BF4)26H2O (0.10 mmol) in dry methanol(2 mL), Ar gas aerated for 5 min, was added to a stirred solutionof <strong>[16858-01-8]tpa</strong> (0.10 mmol) in dry MeOH solution (5 mL) and the resultingsolution was stirred for 30 min. A solution of Et3N (0.20 mmol) andH4L1 (0.050 mmol) in Et2O (7 mL), Ar gas aerated for 15 min, wasadded to the above methanol solution slowly. The solution wasallowed to stand at 13 C for 3 days to obtain the desired complexas a dark green precipitate. The yield obtained was 47%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.3% | With ammonium hydroxide; N,N-dibutylpyrrolidinium bromide; at 40℃; for 1h; | General procedure: Put 10g of 2-chloromethylpyridine in a 100ml three-neck reaction flask, add 30 ml of the ionic liquid prepared in Example 1, slowly add 30% wt ammonia water at 40 C, the reaction was monitored by TLC. After the 2-chloromethylpyridine reaction was completed, the reaction was stirred for an additional hour. Stop the reaction, drop to room temperature, slowly add deionized water, until the precipitate no longer precipitates, filter, and use 5wt% Na2CO3 solution, washed with ethanol and dried to give 5.7 g of tris(pyridine-2-ylmethyl)amine, the yield was 97.3% and the purity was 98.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In methanol; at 20℃; for 3h; | In a 10 mL round bottom flask 27.5 mg (0.125 mmol) of Zn(OAc)2*2H2O and 36.5 mg (0.125 mmol) of <strong>[16858-01-8]tpa</strong> was dissolved in 3 mL methanol. To this 14 mg (0.125 mmol) of acetylene dicarboxylic acid was added. The reaction mixture was stirred for another 3 h at room temperature. The resulting slurry was evaporated to dryness, treated with 2 mL of acetonitrile-toluene mixture (50:50 v/v) to completely remove the acetic acid affording a pure solid. Yield: 42 mg (64%). Anal.Calcd for C44H46N8Zn2O13 (MW 1025.63): Calc. C, 51.48; H, 4.48; N,10.92. Found: C, 52.51; H, 4.94; N, 10.93. Selected FTIR peaks (KBr,cm-1): 3411, 1610, 1483, 1340, 1024, 778, 651. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In methanol; at 20℃; for 3h; | In a 10 mL round bottom flask 33.5 mg (0.125 mmol) of Cd(OAc)2*2H2O and 36.5 mg (0.125 mmol) of <strong>[16858-01-8]tpa</strong> was dissolved in in 3 mL methanol. To this 14 mg (0.125 mmol) of acetylene dicarboxylic acid was added. The reaction mixture was stirred for another 3 h at room temperature. The resulting slurry was evaporated to dryness, treated with 2 mL of acetonitrile-toluene mixture (50:50 v/v) to completely remove the acetic acid affording a pure solid. Yield: 46 mg (72%). Single crystals were obtained by the slow evaporation of its aqueous solution. Anal. Calcd for C22H18N4Cd1O4 (MW 514.80): Calc. C, 51.33;H, 3.52; N, 10.88. Found: C, 50.71; H, 3.45; N, 10.68. Selected FTIR peaks (KBr, cm-1): 3409, 1616, 1581, 1476, 1363, 1013, 777, 674. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | General procedure: Under N2 atmosphere, methanol solution (2 mL) of Zn(ClO4)2·6H2O (51 mg, 1.37 × 10-4 mol) was added to methanol solution (2 mL) of chelating ligand L (1.37 × 10-4 mol), and the mixture was stirred until L fully dissolved. In dark condition, the solution was added to methanol solution (2 mL) containing CO-releasingunit R (1.37 × 10-4 mol) and Me4NOH·5H2O (25 mg,1.37 × 10-4 mol). The mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure,and the obtained solid dissolved in CH2Cl2. The solution was then filtered through a Celite/glass wool plug, and the final product was precipitated by addition of ethyl ether. All the solid products were dried under reduced pressure(Scheme 3). [(<strong>[16858-01-8]TPA</strong>)Zn(4-N(Et)2FLH)]ClO4 (5a): Yield: 76%. 1HNMR (DMSO-d6, 400 MHz): 9.31 (s, 3H), 8.87-8.56 (m,6H), 8.11 (t, 3H), 7.32 (t, 2H), 7.09 (m, 2H), 6.69 (d, 2H),6.34 (d, 2H), 4.56 (s, 6H), 3.85 (s, 4H), 1.15 (s, 6H); 13CNMR (DMSO-d6, 100 MHz): delta 158.46, 147.48, 144.21,142.36, 129.18, 127.36, 125.61, 124.95, 123.51, 118.86,114.96, 112.73, 51.58, 46.36,13.43. ESI-MS: m/z ([(<strong>[16858-01-8]TPA</strong>)Zn(4-N(Et)2FLH)]+) = 662.2145, Calcd: 662.2110. FTIR(KBr, cm-1): 1600 (nuC=O), 1090 (nuClO4), 619 (nuClO4). Anal.Calcd for C37H36N5O3ZnClO4:C, 58.2; H, 4.7; N, 9.2.Found: C, 58.2; H, 4.7; N, 9.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | General procedure: Under N2 atmosphere, methanol solution (2 mL) of Zn(ClO4)2·6H2O (51 mg, 1.37 × 10-4 mol) was added to methanol solution (2 mL) of chelating ligand L (1.37 × 10-4 mol), and the mixture was stirred until L fully dissolved. In dark condition, the solution was added to methanol solution (2 mL) containing CO-releasingunit R (1.37 × 10-4 mol) and Me4NOH·5H2O (25 mg,1.37 × 10-4 mol). The mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure,and the obtained solid dissolved in CH2Cl2. The solution was then filtered through a Celite/glass wool plug, and the final product was precipitated by addition of ethyl ether. All the solid products were dried under reduced pressure(Scheme 3). [(<strong>[16858-01-8]TPA</strong>)Zn(4-N(Me)2FLH)]ClO4 (1a): Yield: 80%. 1HNMR (DMSO-d6, 400 MHz): 9.13 (s, 3H), 8.68-8.37(m, 6H), 8.01 (t, 3H), 7.21 (t, 2H), 7.10 (m, 2H), 6.79(d, 2H), 6.56 (d, 2H), 4.66 (s, 6H), 2.85 (s, 6H); 13CNMR (DMSO-d6, 100 MHz): delta 157.36, 148.47, 143.61,142.16, 129.88, 127.66, 126.61, 124.85, 123.40, 117.86,113.96, 112.23, 50.58, 43.36. ESI-MS: m/z ([(<strong>[16858-01-8]TPA</strong>)Zn(4-N(Me)2FLH)]+) = 634.1827, Calcd: 634.1797. FTIR (KBr,cm-1): 1600 (nuC=O), 1090 (nuClO4), 619 (nuClO4). Anal. Calcdfor C35H32N5O3ZnClO4:C, 57.2; H, 4.4; N, 9.5. Found: C,57.2; H, 4.3; N, 9.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.8% | In methanol; dichloromethane at 20℃; for 0.5h; | [CuCl2(TPA)]. A solution of TPA (0.073 g, 0.25 mmol) in 2 mL of methanol was added to a suspension of CuCl2·2H2O (0.043 g, 0.25 mmol) in 2 mL of CH2Cl2 to produce a light green solution. After stirring for 30 min at room temperature, diethyl ether (30 mL) was slowly added to precipitate the product. Green powder was then filtered, washed with pentane (3×10 mL) and dried under vacuum to yield 0.092 g (86.8%) of [CuCl2(TPA)]. Crystals were obtained by slow diffusion of diethyl ether into an acetonitrile solution of the copper(II) complex at ambient temperature. Elemental analysis: calcd for C18H18Cl2CuN4·H2O: C 48.82, H 4.55, N 12.65%; found: C 48.91, H 4.53, N 12.57%; ESI-MS: m/z calcd for C18H18Cl2CuN4: [CuCl(TPA)]+ 388.05; found 387.90; FT-IR (KBr): γmax (cm-1): 3394, 3063, 3030, 2938, 1606, 1571, 1479, 1439, 1368, 1307, 1262, 1158, 1096, 1050, 1020, 978, 956, 883, 841, 778, 733, 644, 506, 481, 411. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In methanol at 20℃; for 0.5h; | [ZnCl2(TPA)]. A solution of TPA (0.073 g, 0.25 mmol) in 2 mL of methanol was added to a suspension of ZnCl2 (0.034 g, 0.25 mmol) in 2 mL of methanol to produce a colourless solution. After stirring for 30 min at room temperature, diethyl ether (30 mL) was slowly added to precipitate the product. White powder was then filtered, washed with pentane (3×10 mL) and dried under vacuum to yield 0.096 g (90.0%) of [ZnCl2(TPA)]. Crystals were obtained by slow diffusion of diethyl ether into a methanol solution of the zinc(II) complex at ambient temperature. Elemental analysis: calcd for C18H18Cl2ZnN4·0.5H2O: C 49.63, H 4.40, N 12.86%; found: C 49.72, H 4.43, N 12.89%; ESI-MS: m/z calcd for C18H18Cl2ZnN4: [ZnCl(TPA)]+ 389.05; found 388.85; FT-IR (KBr): γmax (cm-1): 3576, 3506, 3080, 3029, 2924, 1607, 1572, 1483, 1436, 1372, 1316, 1295, 1269, 1244, 1155, 1127, 1101, 1052, 1024, 964, 912, 896, 838, 782, 765, 734, 649, 505, 475, 415. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.4% | In acetonitrile at 20℃; for 1h; | [FeCl3(TPA)]. A solution of TPA (0.202 mg, 0.69 mmol) in 2 mL of MeCN was added to a suspension of FeCl3 (0.112g, 0.69 mmol) in 5 mL of MeCN to produce a reddish suspension. After stirring at room temperature for 1 hour, the reaction mixture was filtered to yield a light red solution. Diethyl ether (30 mL) was slowly added to the filtrate to precipitate the product. Yellow powder was then filtered, washed with diethyl ether (3×10 mL) and dried under vacuum to yield 0.254 g (81.4%) of [FeCl3(TPA)]. Colorless single crystals were obtained by slow diffusion of diethyl ether into a methanol solution of the iron (III) complex at ambient temperature. Elemental analysis: calcd for C18H18Cl3FeN4·2CH3OH: C 46.68, H 4.70, N 10.89%; found: C 46.65, H 4.56, N 10.98%; ESI-MS: m/z calcd for C18H18N4: [Fe(TPA)(CH3O)2]+ 408.13; found 407.95; FT-IR (KBr): γmax (cm-1): 3395, 3105, 3070, 3029, 2927, 1651, 1606, 1570, 1484, 1442, 1289, 1159, 1096, 1053, 1024, 912, 766, 731, 648, 518, 500, 477, 419. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In methanol at 20℃; for 1h; | [CoCl2(TPA)]. A solution of TPA (0.035 g, 0.27 mmol) in 2 mL of methanol was added to a solution of CoCl2 (0.079g, 0.27 mmol) in 2 mL of methanol to produce a greenish solution. After stirring for 30 min at room temperature, diethyl ether (30 mL) was added to force the coordination complex out of solution to form a viscous oil. Excess supernatant was decanted and the oil dried under vacuum to form a green solid. Recrystallization was affected by redissolving in CH2Cl2 and carefully layering in diethyl ether to form a cloudy solution. The solution was allowed to stand overnight at room temperature, producing green crystals (0.085 g, 89.0%). Elemental analysis: calcd for C18H18Cl2N4Co·1.5H2O: C, 48.34; H, 4.73; N, 12.53. Found: C, 48.29; H, 4.75; N, 12.57%; ESI-MS: m/z calcd for C18H18Cl2CoN4: [CoCl(TPA)]+ 384.06; found 383.90; FT-IR (KBr): γmax (cm-1): 3399, 3065, 3030, 2920, 1645, 1608, 1569, 1482, 1439, 1370, 1311, 1265, 1160 1102, 1053, 1024, 980, 963, 837, 778, 733, 650, 505, 476, 415. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In acetonitrile for 2.5h; | |
80% | In methanol for 0.5h; | [NiCl2(TPA)]. A hot solution of NiCl2·6H2O (0.059 g, 0.25 mmol) in 2 mL of ethanol was added with stirring to a solution of the A solution of TPA (0.073 g, 0.25 mmol) in 2 mL of methanol. After stirring for 30 min, diethyl ether (30 mL) was slowly added to precipitate the product. Blue powder was then filtered, washed with pentane (3×10 mL) and dried under vacuum, and recrystallised from ethanol-diethyl ether mixture solvent. The blue initial product obtained contained one molecule of ethanol per metal atom. On heating the blue crystals in refluxing acetone the green complex, [NiCl2(TPA)], was obtained. Yield: 0.084 g (80.0%). Elemental analysis: calcd for C18H18Cl2NiN4·H2O: C 49.36, H 4.60, N 12.79%; found: C 49.44, H 4.63, N 12.82%; ESI-MS: m/z calcd for C18H18Cl2NiN4: [Ni(TPA)Cl]+ 383.06; found 382.90; FT-IR (KBr): γmax (cm-1): 3401, 3065, 3028, 2932, 1628, 1605, 1571, 1481, 1442, 1427, 1352, 1314, 1289, 1153, 1098, 1050, 1022, 995, 978, 957, 942, 912, 821, 777, 764, 645, 518, 476, 421. |
70% | In methanol for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: copper(II) perchlorate hexahydrate; tris[(2-pyridylmethyl)amine] In acetonitrile at 30℃; for 0.5h; Inert atmosphere; Glovebox; Stage #2: 2-chloro-1,3-bis(4′-methyl-phenyl)-1,3-propanedione With lithium hexamethyldisilazane In diethyl ether; acetonitrile at 30℃; for 16h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: copper(II) perchlorate hexahydrate; tris[(2-pyridylmethyl)amine] In acetonitrile at 30℃; for 0.5h; Inert atmosphere; Glovebox; Stage #2: acetonitrile; lithium hexamethyldisilazane; 2-chloro-1,3-bis(4′-methoxy-phenyl)-1,3-propanedione In diethyl ether at 30℃; for 16h; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | Stage #1: 2-(chloromethyl)pyridine hydrochloride With sodium hydroxide In lithium hydroxide monohydrate at 0 - 4℃; Stage #2: (2-aminomethylpyridine) In dichloromethane; lithium hydroxide monohydrate at 20℃; for 48h; Cooling with ice; | 5.2.1 Synthesis of TPMA ligand The current synthesis is an adaptation of the literature procedure [86]. 2-(chloromethyl)pyridine hydrochloride (39g, 238mmol) was dissolved in 100mL of water in a 500mL round-bottomed flask and this solution was chilled overnight in the fridge (4°C) together with 100mL of 5.3M NaOH solution. Flask with chilled hydrochloride solution was placed in the ice bath (0°C) and cold 5.3M NaOH solution (45mL total) was added in 5mL portions. The last addition caused the reaction mixture to turn slightly red. Addition of 1mL of 5.3M NaOH resulted in a permanent red coloration. To this mixture a solution of 2-(aminomethyl)-pyridine in 200mL DCM was added in one portion and flask was removed from the ice bath to warm up to room temperature. Next, 5.3M NaOH was added dropwise on vigorous stirring at a very low rate (2mL/h.) to keep the reaction mixture pH below 9.5. Reaction was stirred very intensely for 48h. The mixture was then diluted with 100mL of 15 % aqueous NaOH solution and organic phase was separated, dried over anhydrous MgSO4 and evaporated to a brown oil. This was extracted 4x100 ml of boiling diethyl ether. An oily residue that was not extracted into Et2O was discarded. The collected extracts were evaporated to an oil, dissolved in ethyl acetate and precipitated with 60/90 petroleum ether. This off-white solid was collected on a G3 glass funnel, washed with petroleum ether and dried to give pure product. Yield: 9.27g (27 %). 1HNMR (MeCN-d3): 8.47 (m, 3H), 7.70 (m,3H), 7.59 (m,3H), 7.20 (m,3H), 3.81 (s,6H) (Fig. S20). |
Tags: 16858-01-8 synthesis path| 16858-01-8 SDS| 16858-01-8 COA| 16858-01-8 purity| 16858-01-8 application| 16858-01-8 NMR| 16858-01-8 COA| 16858-01-8 structure
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