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CAS No. : | 950984-75-5 | MDL No. : | MFCD30833928 |
Formula : | C15H15N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UKLHHECOZJWQJN-UHFFFAOYSA-N |
M.W : | 237.31 | Pubchem ID : | 101448398 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
94% | Stage #1: Propargylamine With potassium carbonate In acetonitrile for 0.0833333h; Stage #2: 2-chloromethylpyridine hydrochloride In acetonitrile for 120h; Reflux; | |
93% | Stage #1: Propargylamine With potassium carbonate In acetonitrile for 0.0833333h; Stage #2: 2-chloromethylpyridine hydrochloride In acetonitrile for 120h; Reflux; | |
32% | In methanol; water at 65℃; Inert atmosphere; |
In methanol; water at 65℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate In tetrahydrofuran; toluene at 20℃; Inert atmosphere; | |
100% | With potassium carbonate In tetrahydrofuran; toluene at 20℃; | 2.5 5.2.5 (N, N-Bis(2-pyridylmethyl)-N-propargylamine) (5) To a solution of Bis (2-picolyl) amine (BPA) (100 mg, 0.5 mmol) in THF (3 mL) was added propargyl bromide (80% in toluene) (0.1 mL, 0.78 mmol) followed by addition of K2CO3 (207 mg, 1.5 mmol). The mixture was stirred at room temperature until the starting material had completely disappeared as judged by TLC. After removing the solvent under reduced pressure, the residue was purified by column chromatography (CH2Cl2/MeOH=40:1) to give compound 5 (118 mg, 0.5 mmol, 100%) as yellow oil. 1H NMR (400 MHz, CDCl3): δ 8.57 (dd, J=4.9, 0.8 Hz, 2H), 7.67 (td, J=7.7, 1.8 Hz, 2H), 7.53 (d, J=7.8 Hz, 2H), 7.17 (dd, J=6.4, 5.1 Hz, 2H), 3.94 (s, 4H), 3.44 (d, J=2.3 Hz, 2H), 2.30 (t, J=2.4 Hz, 1H). |
96% | With potassium carbonate In tetrahydrofuran at 20℃; for 16h; |
96% | With potassium carbonate In tetrahydrofuran; toluene for 16h; Inert atmosphere; | N-propargyl-dl-(2-picolyl)amine(2)8: Di-(2-picolyl)amine (5.0 mmol, 900 µL)was dissolved in THF (10 mL). K2CO3 (20 mmol, 2.76 g) wasadded followed by dropwise addition of propargyl bromide (80% in toluene, 5.0mmol, 557 µL). The reaction mixture was stirred for 16 hrs before diluted withDCM. The diluted reaction mixture was filtrated through a pad of K2CO3under vacuum before concentrated. Compound 2was isolated in 96% yield from an alumina column elutedby EtOAc in DCM (0% - 40%). 1H-NMR(500 MHz, CDCl3, ppm) δ = 8.52(m, 2H), 7.62 (td, J = 2.0, 7.5 Hz, 2H), 7.47 (d, J= 8.0 Hz, 2H), 7.12 (td, J = 1.0, 5.0Hz, 2H), 3.88 (s, 4H), 3.37 (d, J =2.0 Hz, 2H), 2.27 (t, J = 2.5 Hz,1H); 13C-NMR (125 MHz, CDCl3,ppm) δ =153.6, 129.6, 83.6, 45.2, 34.6, 32.3, 26.5, 24.9. |
96% | With potassium carbonate In toluene; acetonitrile for 24h; | |
89% | With potassium carbonate In toluene; acetonitrile for 12h; Reflux; | |
87% | With potassium carbonate In acetone at 70℃; | |
87% | With potassium carbonate In acetonitrile | 1 Typically 1 -(Chloromethyl)-4-nitro- 1R-Imidazole (2) was obtained by reacting 4-nitro-1R-Imidazole (1) with paraformaldehyde in the presence of thionyl chloride in chloroform. 1 -(Azidomethyl)-4-nitro- 1R-imidazole (3) was synthesized by reacting 1 -(Chioromethyl)-4-nitro- 1R-Imi- dazile (2) with sodium azide in DMF at 50° C. The reaction of di-(2-picolyl) amine with propargyl bromide in the presence of potassium carbonate in acetonitrile gave the propargyl di (2-picolyl) amine (4) in 87% yield [Click reactions with this compound and different arylazides (benzyl-, anthracenyl- or anthracenylmethylazide) gave the N,N’-bis (2-pyridylmethyl)-N”-(4-triazolylmethyl)amino tripodal chelating system in 26-60% yield”, A Click procedure with heterogeneous copper to tether technetium-99m chelating agents and rhenium complexes. Evaluation of the chelating properties and biodistribution of the new radiolabelled glucose conjugates. Eric l3enoist, Yvon Coulais, Mehdi Almant, Jose Kovensky, Vincent Moreau, David Lesur, Marine Artigau, Claude Picarda, Chantal Galaup, Sbastien G. Gouin. Carbohydrate Research, Volume 346, Issue 1, 2011, Pages 26-34, [7] and Eric l3enoist et al., “A Click procedure with heterogeneous copper to tether technetium-99m chelating agents and rhenium complexes. Evaluation of the chelating properties and biodistribution of the new radiolabelled glucose conjugates”, Carbohydrate Research, Volume 346, Issue 1, 3 Jan. 2011, Pages 26-34], [8] 4-nitro-111-Imida- zole-methyl-1 ,2,3-triazol-methyl-di-(2-pycolyl) amine (5) was obtained by the dissolution in a mixture of solvents dioxane/water at 1000 C. of propargyl-di (2-picolyl) amine (4) with 1-(azidomethyl)-4-nitro-1H-imidazole (3) in the presence of copper sulphate, sodium ascorbate. |
86% | With potassium carbonate In tetrahydrofuran for 3h; Reflux; | 1 Example 1 - Synthesis of N,N'-dipicolyl-N-propagyl amine. Example 1 - Synthesis of N,N'-dipicolyl-N-propagyl amine. N^V-dipicolylamine (5,0 mL, 22,9 mmol, 1 ,0 eq.) was diluted in THF (55,7 mL, 700 mmol, 25 eq.) followed by addition of K2C03 (15,40 g, 1 1 1 ,4 mmol, 4,0 eq.) and propagyl bromide (4,34 mL 80%, 39,0 mmol, 1 ,4 eq.). The mixture was heated to reflux under heavy stirring and left for three hours. The deep red slurry was then cooled down to room temperature, filtered using a glass filter, the filter washed with 2x20 mL dichloromethane and the combined organic phases were concentrated under reduced pressure to a rust-red oil. The crude product was purified using column chromatography and the product was eluted from an alumina column by methanol in dichloromethane (1-5%) yielding 5.55 g (86%). FontWeight="Bold" FontSize="10" H and 13C NMR are in accordance with published results. |
84% | With potassium carbonate In tetrahydrofuran; toluene at 70℃; Inert atmosphere; | |
82% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; | 1.2 (2) Synthesis of 4'-{4-[N,N-bis (2-pyridylmethyl)]methylene-1H-1,2,3-triazolyl}-2,2’:6’,2”-bitripyridine-6,6"-dimethylaminetetraacetic acid tert-butyl ester (compound 3) 2.1. 100 mg (0.50 mmol) of bis (2-pyridylmethyl) amine,72 mg of propargyl bromide (0.61 mmol) and 150.8 mg (1.09 mmol) of K2CO3 were dissolved in 5 mL of anhydrous DMF, and the reaction product 2 was obtained by stirring at room temperature for 12 hours.2.2. Add 10 mL of water to reaction product 2 in step 2.1, extract with 3 × 20 mL of ethyl acetate, and dry with anhydrous Na 2 SO 4 to obtain the crude product.2.3. The crude product from step 2.2 was dried and separated on silica gel column chromatography using ethyl acetate and petroleum ether (1: 2, v / v) as eluents.The main product was collected and dried under vacuum to obtain 97.2 mg of a brown oil as an intermediate product with a yield of 82.0% |
78% | With potassium carbonate In tetrahydrofuran at 20℃; for 6h; | |
73% | With triethylamine In toluene for 24h; Heating; | |
64% | With triethylamine In toluene for 23h; Reflux; Inert atmosphere; | N,N-bis(pyridin-2-ylmethyl)prop-2-yn-1-amine(DPA-alkyne, 7a) To a solution of bis(2-picolyl)amine (1.000 g, 5.02 mmol)in toluene (50 mL), propargyl bromide (80 wt% in toluene,0.70 mL, 7.86 mmol) and triethylamine (0.75 mL,5.38 mmol) were added. The reaction mixture was refluxedfor 23 h, during which time a brown solid precipitated. Thesolid was removed via vacuum filtration, and the filtratewas concentrated under reduced pressure. The compoundwas purified by column chromatography on silica gel usingDCM/ACN/NH4OH (5:5:0.1) as eluent. The solvent wasremoved by evaporation under reduced pressure, yielding adark brown oil. Yield: 0.766 g (64%). 1H NMR (400 MHz,Chloroform-d) δ 8.27 (d, J = 4.9 Hz, 2H), 7.40-7.31 (m,2H), 7.24 (d, J = 7.8 Hz, 2H), 6.90-6.81 (m, 2H), 3.65 (s,4H), 3.17-3.12 (m, 2H), 2.10 (q, J = 2.0 Hz, 1H). MS: m/z238 (M + 1). |
63% | With potassium carbonate; potassium iodide In acetonitrile Reflux; Inert atmosphere; | 2.2.2. 2-((Prop-2-yn-1-yl(pyridin-2-ylmethyl)amino)methyl)phenol(B) General procedure: To a solution of 2-(((pyridin-2-ylmethyl)amino)methyl)phenol(2.56 g, 11.23 mmol) in MeCN (100mL), K2CO3 (1.56 g, 11.28 mmol),KI (1.88 g, 11.34mmol) and propargyl bromide (1.37 g, 11.5mmol)were added. After being refluxed for 24 h, the reacted mixture was cooled to room temperature and then filtered. The filtrate was removed of solvent under reduced pressure to give a crude product, which was further purified using flash chromatography on silica gel column with ethyl acetate as eluent to give a yellowoily liquid (1.83 g, 65%). |
58% | With potassium carbonate In tetrahydrofuran for 24h; Reflux; | |
42% | With potassium carbonate In tetrahydrofuran at 20℃; Inert atmosphere; | |
With potassium carbonate In tetrahydrofuran; toluene at 20℃; for 48h; Inert atmosphere; | ||
With potassium carbonate In acetonitrile | ||
With potassium carbonate In tetrahydrofuran Reflux; | ||
With potassium carbonate In tetrahydrofuran at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper diacetate In methanol; water at 20℃; for 18h; | |
60% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; | |
41% | With copper(l) iodide; triethylamine In tetrahydrofuran at 40℃; for 18h; |
With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 1.5h; | ||
0.702 g | With 3-butyl-1-isopropyl-1H-benzo[d]imidazol-3-ium bromide; copper(l) iodide; potassium <i>tert</i>-butylate In dichloromethane at 20℃; for 72h; Inert atmosphere; | |
With copper(II) sulfate; sodium L-ascorbate In water; acetone at 50℃; for 1h; Microwave irradiation; | 4.2.1 General procedure for the synthesis of 4a-g General procedure: 2 (1 eq), 3a-d (1.1 eq), Na ascorbate (0.8 eq) and CuSO4 (0.4 eq) were dissolved in a mixture 1:1 acetone and water (0.2 M). The reaction was performed by microwave at 50 °C for 1 h. The reaction mixture was extracted with ethyl acetate and the collected organic layers were washed with NH3 1 M and dried with sodium sulfate. The solvent was evaporated under vacuum to give the crude which was purified by column chromatography (AcOEt/Hexane 4:6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; | |
88% | With copper diacetate In methanol; water at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; N,N',N''-tris(2-benzimidazolylmethyl)amine In water; dimethyl sulfoxide at 110℃; for 24h; Sealed tube; | |
43% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In methanol room temp., 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; n-heptane 90°C, 16 h; water was added; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In methanol room temp., 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In methanol room temp., 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In methanol room temp., 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In methanol room temp., 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol room temp., 1 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With copper diacetate In water; <i>tert</i>-butyl alcohol at 20℃; for 18h; | |
With copper(II) sulfate; sodium L-ascorbate In water; acetone at 50℃; for 1h; Microwave irradiation; | 4.2.1 General procedure for the synthesis of 4a-g General procedure: 2 (1 eq), 3a-d (1.1 eq), Na ascorbate (0.8 eq) and CuSO4 (0.4 eq) were dissolved in a mixture 1:1 acetone and water (0.2 M). The reaction was performed by microwave at 50 °C for 1 h. The reaction mixture was extracted with ethyl acetate and the collected organic layers were washed with NH3 1 M and dried with sodium sulfate. The solvent was evaporated under vacuum to give the crude which was purified by column chromatography (AcOEt/Hexane 4:6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With copper diacetate In methanol; water at 20℃; for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With copper diacetate In methanol; water at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With copper diacetate In methanol; water at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper diacetate In methanol; water at 20℃; for 18h; | |
With copper(II) sulfate; sodium L-ascorbate In water; acetone at 50℃; for 1h; Microwave irradiation; | 4.2.1 General procedure for the synthesis of 4a-g General procedure: 2 (1 eq), 3a-d (1.1 eq), Na ascorbate (0.8 eq) and CuSO4 (0.4 eq) were dissolved in a mixture 1:1 acetone and water (0.2 M). The reaction was performed by microwave at 50 °C for 1 h. The reaction mixture was extracted with ethyl acetate and the collected organic layers were washed with NH3 1 M and dried with sodium sulfate. The solvent was evaporated under vacuum to give the crude which was purified by column chromatography (AcOEt/Hexane 4:6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | In not given mixing nitrogen compd., rhenium complex, heating at 70°C for 2 h; isolation of solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With CuI; sodium ascorbate In H2O; dimethylsulfoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | With sodium azide; copper(ll) sulfate pentahydrate; ascorbic acid In water; N,N-dimethyl-formamide for 8h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Stage #1: N-propargyl-N,N-bis(2-pyridylmethyl)amine; 2-azido-N-(4-nitro-3-(trifluoromethyl)phenyl)acetamide With copper diacetate; sodium L-ascorbate In methanol; water at 20℃; for 12h; Stage #2: With ethylenediaminetetraacetic acid In methanol; water for 0.5h; Stage #3: With potassium hydroxide In methanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper nanoparticles on activated carbon In water; <i>tert</i>-butyl alcohol at 100℃; for 0.25h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate In ethanol; water at 20℃; for 12h; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; | 2. Synthesis of 1 2 (2.13 g, 4.8 mmol) and 3 (2.39 g, 10.12 mmol) were dissolved in DMF (100 mL). Aqueous CuSO4·5H2O (48 mg, 2 mol %) solution (25 mL) were added, then sodium ascorbate (190 mg, 10 mol%) were added under an atmosphere of argon. The reaction mixture was stirred at room temperature for 24h.The resulting solution was added to a solution of saturated sodium bicarbonate with a minimal amount of ammonium hydroxide. The aqueous solution was then extracted with ethyl acetate and washed with brine. After drying the organic solution over Na2SO4, the crude material was purified by column chromatography (EtOAc /MeOH,15/1, v/v) as a pale oil which was purified further by recrystallization (EtOAc) to give 1 as a white solid in 68% yield ( 2.92 g, 3.21 mmol ); m.p.: 141-142°C. 1H NMR (CDCl3, 500 MHz)δ: 8.54(d, J = 4.5 Hz, 4H), 7.65(td, J = 7.5, 1.5 Hz, 4H), 7.56(d, J = 7.8 Hz, 4H), 7.51(s, 2H), 7.15(dd, J = 5.0Hz, 6.5Hz, 4H), 7.08(m, 6H), 6.9(m, 12H), 5.42(s, 4H),3.89 (s, 4H),3.85 (s, 8H); 13C NMR (125 MHz, CDCl3) δ:159.2, 149.0, 144.6, 143.8, 143.0, 140.7, 136.4, 133.0, 131.8, 131.1, 127.8, 127.2, 126.8, 123.3, 123.0, 122.0, 59.6, 53.6, 48.6; ESI-MS:m/z (%): 917(60) [M+H+], 939(100) [M+Na+], 955(2)[M+K+]. Element analysis (%) Calca. For C58H52N12: C, 75.96; H, 5.71; N, 18.33. Found: C, 75.99; H, 5.67; N, 18.34. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With sodium L-ascorbate; copper(l) chloride In tetrahydrofuran at 60℃; for 4.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(II) acetate monohydrate; sodium L-ascorbate In methanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper In <i>tert</i>-butyl alcohol at 20℃; for 24h; Inert atmosphere; | Synthesis of LtBu LtBu was prepared according to the previous report. The mixture of 1 (500 mg, 2.1 mmol), tBuN3 (500 mg, 5.0 mmol), and copper(0) powder (1.0 g) was stirred in 2-methyl-2-propanol (=tBuOH, 10 mL) for 24 h under N2 at room temperature. The copper powder was removed by filtration and the solvent was evaporated under reduced pressure. Purification of the residue on an alumina column eluted by ethyl acetate yielded LtBu as a yellow solid (566 mg, 80% yield). |
80% | With copper In <i>tert</i>-butyl alcohol at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In aq. phosphate buffer at 70℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With copper diacetate; sodium L-ascorbate In methanol; aq. phosphate buffer at 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: N-propargyl-N,N-bis(2-pyridylmethyl)amine; fac-[99mTcI(OH2)3(CO)3](1+) In aq. phosphate buffer at 70℃; Inert atmosphere; Sealed tube; Stage #2: C60H87N21O13S With sodium L-ascorbate In aq. phosphate buffer for 0.0833333h; Inert atmosphere; Sealed tube; Stage #3: With copper diacetate In aq. phosphate buffer at 50℃; for 1h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In aq. phosphate buffer at 70℃; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In methanol for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: Propargylamine With potassium carbonate In acetonitrile for 0.0833333h; Stage #2: 2-chloromethylpyridine In acetone for 120h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol / 6 h 1.2: 20 °C 2.1: potassium carbonate / tetrahydrofuran / 24 h / Reflux | ||
Multi-step reaction with 3 steps 1: methanol / 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 20 °C / Inert atmosphere 3: potassium carbonate; potassium iodide / acetonitrile / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol / 6 h 1.2: 20 °C 2.1: potassium carbonate / tetrahydrofuran / 24 h / Reflux | ||
Multi-step reaction with 3 steps 1: methanol / 20 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 20 °C / Inert atmosphere 3: potassium carbonate; potassium iodide / acetonitrile / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With copper(l) iodide; triethylamine In acetonitrile Inert atmosphere; Reflux; | Ligand H2LI General procedure: To a solution of 2-((prop-2-yn-1-yl(pyridin-2-ylmethyl)amino)methyl)phenol (151.2 mg, 0.6 mmol) in MeCN (80 mL), 2,6-bis(azidomethyl)pyridine (56.7 mg, 0.3 mmol), CuI (6 mg, 0.03 mmol) and Et3N (0.4 mL, 0.36 mmol) were added under Ar atmosphere. After being refluxed for two days under the continually stirring, the mixture was cooled to room temperature. Removal of the solvent under reduced pressure gave a crude product which was further purified using flash chromatography on silica gel column with ethyl acetate as eluent to give a light brown solid (75.17 mg,36%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 20 °C / Inert atmosphere 2: potassium carbonate; potassium iodide / acetonitrile / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(II) acetate monohydrate; sodium L-ascorbate In water; acetonitrile for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With copper(II) sulfate heptahydrate; sodium L-ascorbate In tert-butyl methyl ether; water; <i>tert</i>-butyl alcohol at 20℃; for 16h; | 2; 3 Example 2 - General procedure for the synthesis of triazoles General procedure: Example 2 - General procedure for the synthesis of triazoles Copper sulfate heptahydrate (250 mg, 1.0 mmol, 1.0 eq.) in 2.5 mL H20 and sodium (+)ascorbate (396 mg, 2,0 mmol, 2.0 eq.) in 2.5 mL H20 were added simultaneously to a stirring solution of the alkyne (1.0 mmol, 1.0 eq.) in 2.5 mL iBuOH. The azide solution (4.0 mL 25% in iBuOMe, 1.0 mmol, 1.0 eq) was then added and the solution was stirred at room temperature for 16 hours. EDTA (293 mg, 1.0 mmol, 1.0 eq) was then added to the stirring solution and left for 60 minutes before the mixture was diluted with 50 mL H20 and the pH of the mixture was adjusted to >10 with 1M NaOH. The slurry was then extracted with 50 mL EtOAc and 50 mL dichloromethane. The combined organic phases were dried over K2C03 and concentrated under reduced pressure to give a dark red oil/semisolid. The crude products were purified using column chromatography by eluting a neutral A1203 column with 1-10% methanol in dichloromethane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; | 33 Example 33 - Preparation of Methyl (2-(4-((bis(pyridin-2-ylmethyl)amino)methyl)- 1 H- 1 ,2,3-triazol- 1 -y^acety -D-alanyl-TJ-alaninate. Example 33 - Preparation of Methyl (2-(4-((bis(pyridin-2-ylmethyl)amino)methyl)- 1 H- 1 ,2,3-triazol- 1 -y^acety -D-alanyl-TJ-alaninate. Copper acetate (200 mg, 1.0 mmol, 1.0 eq.) in 2.5 mL H20 and sodium-(+)ascorbate (396 mg, 2,0 mmol, 2.0 eq.) in 2.5 mL H20 were added simultaneously to a stirring solution of the alkyne (237 mg, 1.0 mmol, 1.0 eq.) in 2.5 mL iBuOH. The azide prepared in Example 32 (257 mg, 1.0 mmol, 1.0 eq) was then added and the solution was stirred at room temperature for 16 hours. EDTA (293 mg, 1.0 mmol, 1.0 eq) was then added to the stirring solution and left for 60 minutes before the mixture was diluted with 50 mL H20 and the pH of the mixture was adjusted to >10 with 1M NaOH. The slurry was then extracted with 2x50 mL dichloromethane. The combined organic phases were dried over K2C03 and concentrated under reduced pressure to give a dark red oil. The crude products were purified using column chromatography by eluting a neutral A1203 column with 0-5% methanol in dichloromethane to give 134 mg of the title compound as a pale orange oil (27%). 1H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J= 7.5 Hz, 1H), 8.49 (d, J= 4.7 Hz, 2H), 8.43 (d, J= 7.2 Hz, 1H), 8.04 (s, 1H), 7.77 (t, J= 7.7 Hz, 2H), 7.57 (d, J= 7.8 Hz, 2H), 7.29 - 7.21 (m, 2H), 5.13 (s, 2H), 4.42 - 4.21 (m, 2H), 3.77 - 3.70 (m, 6H), 3.62 (s, 3H), 1.31 - 1.21 (m, 6H). 13C NMR (101 MHz, DMSO) δ 172.8, 171.8, 165.0, 159.0, 148.8, 143.1 , 136.5, 125.3, 122.5, 122.1 , 58.7, 51.8, 51.4, 48.0, 47.9, 47.5, 31.3, 18.3, 16.8. HRMS e z calculated for C24H30N8O4: 494.2390, found 495.2463 (M+H). |
27% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; | 194 Example 194 - peptide-based analog - Methyl (2-(4-((bis(pyridin-2- ylmethyl)amino)methyl)lH-l,2,3-triazol-l-yl)acetyl)-D-alanyl-D-alaninate. The compound was prepared as described in WO 2015/049546. Copper acetate (200 mg, 1.0 mmol, 1.0 eq.) in 2.5 mL H20 and sodium-(+)ascorbate (396 mg, 2,0 mmol, 2.0 eq.) in 2.5 mL H20 were added simultaneously to a stirringsolution of the alkyne (237 mg, 1.0 mmol, 1.0 eq.) in 2.5 mL tBuOH. The azideprepared in Example 32 (257 mg, 1.0 mmol, 1.0 eq) was then added and the solutionwas stirred at room temperature for 16 hours. EDTA (293 mg, 1.0 mmol, 1.0 eq) was then added to the stirring solution and left for 60 minutes before the mixture was diluted with 50 mL H20 and the pH of the mixture was adjusted to> 10 with 1M NaOH. The slurry was then extracted with 2x50 mL dichloromethane. The combined organic phases were dried over K2C03 and concentrated under reduced pressure to give a dark red oil. The crude products were purified using column chromatography by eluting a neutral A1203 column with 0-5% methanol in dichloromethane to give 134 mg of the title compound as a pale orange oil (27%). 1H NMR (400 MHz, DMSO-d6) 8 8.59 (d, J= 7.5 Hz, 1H), 8.49 (d, J= 4.7 Hz, 2H), 8.43 (d, J= 7.2 Hz, 1H), 8.04 (s, 1H), 7.77 (t, J= 7.7 Hz, 2H), 7.57 (d, J= 7.8 Hz, 2H), 7.29- 7.21 (m, 2H), 5.13 (s, 2H), 4.42-4.2 l(m,2H), 3.77 - 3.70 (m, 6H), 3.62 (s, 3H), 1.31 - 1.21. (m, 6H). 13C NMR (101 MHz, DMSO) 8 172.8, 171.8, 165.0, 159.0, 148.8, 143.1, 136.5, 125.3, 122.5, 122.1, 58.7, 51.8, 51.4, 48.0, 47.9, 47.5, 31.3, 18.3, 16.8. HRMS e/z calculated for C24H30Ns04: 494.2390, found 495.2463 (M+H). |
27% | With copper diacetate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper diacetate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 16 h / 20 °C 2: lithium hydroxide; water / tetrahydrofuran / 2.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; | 46 Example 46 - Preparation of (2S,5S,6R)-6-(2-(4-((bis(pyridin-2- ylmethyl)amino)methyl)- 1 H- 1 ,2,3-triazol- 1 -yl)acetamido)-3,3-dimethyl-7- thia- 1 -azabicyclo[3.2.0]heptane-2-carboxylic acid. Example 46 - Preparation of (2S,5S,6R)-6-(2-(4-((bis(pyridin-2- ylmethyl)amino)methyl)- 1 H- 1 ,2,3-triazol- 1 -yl)acetamido)-3,3-dimethyl-7- thia- 1 -azabicyclo[3.2.0]heptane-2-carboxylic acid. (2S,5S,6R)-6-(2-azidoacetamido)-3,3-dimethyl-7-oxo-4-thia-l- azabicyclo[3.2.0]heptane-2-carboxylic acid and dipicolyl-propagylamine is dissolved in a mixture of water and tert-butanol. Copper acetate or copper sulfate and (+)- sodium ascorbate are dissolved each in water and simultaneously added drop wise to the stirring mixture. The mixture is then left to stand for 2-7 days at room temperature or until completion. The mixture is then concentrated under reduced pressure and purified by chromatography or recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; | 47 Example 47 - Preparation of (6S,7R)-3-(acetoxymethyl)-7-(2-(4-((bis(pyridin-2- ylmethyl)amino)methyl)-lH-l ,2,3-triazol-l-yl)acetamido)-8-oxo-5-thia-l- azabicyclo[4.2.0]oct-2-en -2-carboxylic acid. Example 47 - Preparation of (6S,7R)-3-(acetoxymethyl)-7-(2-(4-((bis(pyridin-2- ylmethyl)amino)methyl)-lH-l ,2,3-triazol-l-yl)acetamido)-8-oxo-5-thia-l- azabicyclo[4.2.0]oct-2-en -2-carboxylic acid. (6S,7R)-3-(acetoxymethyl)-7-(2-azidoacetamido)-8-oxo-5-thia-l - azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and dipicolyl-propagylamine is dissolved in a mixture of water and teri-butanol. Copper acetate or copper sulfate and (+)-sodium ascorbate are dissolved each in water and simultaneously added drop wise to the stirring mixture. The mixture is then left to stand for 2-7 days at room temperature or until completion. The mixture is then concentrated under reduced pressure and purified by chromatography or recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol 2: potassium carbonate / tetrahydrofuran / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.1% | With copper(II) sulfate; sodium L-ascorbate In water; dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Schlenk technique; | CD-19: N3-b-CD(3.4800 g, 3.0 mmol), 2 (0.3712 g,3.6 mmol), sodium ascorbate (0.1189 g, 0.6 mmol) and CuSO4 (0.0479g, 0.3 mmol) were added under nitrogen atmosphere into a Schlenk tube anddissolved in deaerated DMSO/H2O (v/v, 1/1,40.0 mL). The resulting mixture was stirred at room temperature for 24 h. Afterthe reaction, 20.0 mL of water was added. Poured the mixed solution to acetone(400.0 mL) and the desired triazole functionalized β-CD (CD-1) precipitated. The crude product was obtained by filtration,washed with acetone three times. CD-1was obtained as brown solid powder. Yield: 3.4880 g (92.1%).1H-NMR(500 MHz, DMSO, ppm) δ = 8.49(d, J = 4.0, 2H), 7.98 (s, 1H), 7.77 (td, J = 1.0, 7.5 Hz, 2H), 7.57 (d, J = 8.0 Hz, 2H), 7.25 (t, J = 5.0 Hz, 2H), 5.74 (m, 14H), 4.83 (m,7H) , 4.51 (m, 6H), 3.62 (m, 34H) , 3.38 (m, 7H) , 3.27 (m, 7H); 13C-NMR(125 MHz, DMSO, ppm) δ =159.1, 148.9, 143.4, 136.8, 125.4, 122.8, 122.3, 102.3, 102.1, 82.1, 81.6,73.2, 72.9, 72.5, 72.1, 71.9, 70.1, 60.3, 60.0, 58.8.1H-NMR(500 MHz, D2O, ppm) δ = 8.44(s, 2H), 7.79 (d, J = 3.5 Hz, 2H), 7.72 (s, 1H), 7.49 (d, J = 6.5 Hz, 2H), 7.33 (s, 2H), 5.04 (m, 7H) , 3.84 (m, 34H) , 3.60(m, 14H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium L-ascorbate; copper(II) sulfate / water; <i>tert</i>-butyl alcohol / 12 h / 20 °C 2: piperidine / ethanol / 15 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 12h; | 2.6 5.2.6 9-(4-(4-((Bis(pyridin-2-ylmethyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-9H-carbazole-3-carbaldehyde (6) 18 5.2.6 9-(4-(4-((Bis(pyridin-2-ylmethyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-9H-carbazole-3-carbaldehyde (6) 18 In a mixture of compound 4 (100 mg, 0.32 mmol) and compound 5 (91.3 mg, 0.385 mmol) in water and t-BuOH (v/v=3:1, 4 mL), freshly prepared sodium ascorbate (0.74 mL, 0.2 mol/L) was added, followed by the addition of CuSO4 (1.28 mL, 0.05 mol/L) solution. The heterogeneous mixture was stirred vigorously overnight at room temperature for about 12 h. Then the raw product was washed with distilled water, extracted with DCM, and dried with MgSO4. After removing the solvent with vacuum distillation, the mixture was purified by column chromatography (CH2Cl2/MeOH=20:1) to give compound 6 (82.8 mg, 0.168 mmol, 50%) as yellow solid; mp: 72-73 °C; 1H NMR (400 MHz, CDCl3): δ 10.10 (s, 1H), 8.65 (s, 1H), 8.56 (d, J=4.1 Hz, 2H), 8.19 (d, J=7.7 Hz, 1H), 8.04 (d, J=8.5 Hz, 2H), 7.95 (d, J=8.5 Hz, 1H), 7.69 (dd, J=17.0, 8.0 Hz, 4H), 7.60 (d, J=7.7 Hz, 2H), 7.54-7.33 (m, 5H), 7.20-7.10 (m, 2H), 4.01 (s, 2H), 3.92 (s, 4H). 13C NMR (100 MHz, CDCl3): δ 191.60, 158.94, 149.11, 145.37, 144.16, 141.53, 136.81, 136.61, 136.56, 129.80, 128.42, 127.70, 127.27, 123.83, 123.77, 123.47, 123.38, 122.20, 122.10, 121.62, 121.43, 120.83, 110.17, 109.90, 77.40, 77.08, 76.76, 59.59, 53.44, 48.49. HRMS (ESI): m/z calcd for C34H28N7O [M+H]+: 550.2355, found: 550.2354. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; N,N',N''-tris(2-benzimidazolylmethyl)amine In water; <i>tert</i>-butyl alcohol at 80℃; for 24h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(ll) sulfate pentahydrate; sodium L-ascorbate; N,N',N''-tris(2-benzimidazolylmethyl)amine / water; <i>tert</i>-butyl alcohol / 24 h / 80 °C / Sealed tube; Inert atmosphere 2: dichloromethane; methanol / 0.08 h / Inert atmosphere; Sonication |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(II) sulfate; sodium L-ascorbate In 1,4-dioxane; water at 100℃; | 1 Example 1 Synthesis of 4-Nitro-1 H-Imidazole-Methyl- 1,2,3- Triazol-Methyl-Di-(2-Pycolyl)Amine General procedure: Typically 1 -(Chloromethyl)-4-nitro- 1R-Imidazole (2) was obtained by reacting 4-nitro-1R-Imidazole (1) with paraformaldehyde in the presence of thionyl chloride in chloroform. 1 -(Azidomethyl)-4-nitro- 1R-imidazole (3) was synthesized by reacting 1 -(Chioromethyl)-4-nitro- 1R-Imi- dazile (2) with sodium azide in DMF at 50° C. The reaction of di-(2-picolyl) amine with propargyl bromide in the presence of potassium carbonate in acetonitrile gave the propargyl di (2-picolyl) amine (4) in 87% yield [Click reactions with this compound and different arylazides (benzyl-, anthracenyl- or anthracenylmethylazide) gave the N,N’-bis (2-pyridylmethyl)-N”-(4-triazolylmethyl)amino tripodal chelating system in 26-60% yield”, A Click procedure with heterogeneous copper to tether technetium-99m chelating agents and rhenium complexes. Evaluation of the chelating properties and biodistribution of the new radiolabelled glucose conjugates. Eric l3enoist, Yvon Coulais, Mehdi Almant, Jose Kovensky, Vincent Moreau, David Lesur, Marine Artigau, Claude Picarda, Chantal Galaup, Sbastien G. Gouin. Carbohydrate Research, Volume 346, Issue 1, 2011, Pages 26-34, [7] and Eric l3enoist et al., “A Click procedure with heterogeneous copper to tether technetium-99m chelating agents and rhenium complexes. Evaluation of the chelating properties and biodistribution of the new radiolabelled glucose conjugates”, Carbohydrate Research, Volume 346, Issue 1, 3 Jan. 2011, Pages 26-34], [8] 4-nitro-111-Imida- zole-methyl-1 ,2,3-triazol-methyl-di-(2-pycolyl) amine (5) was obtained by the dissolution in a mixture of solvents dioxane/water at 1000 C. of propargyl-di (2-picolyl) amine (4) with 1-(azidomethyl)-4-nitro-1H-imidazole (3) in the presence of copper sulphate, sodium ascorbate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 60℃; for 24h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate In <i>tert</i>-butyl alcohol for 15h; | 95a Example 95a -tert-Butyl (4-(4-((bis(pyridin-2-ylmethyl)amino)methyl)-lH-l,2,3-triazol- l-yl)phenethyl)carbamate. Sodium ascorbate (10.15 g, 51.24 mmol) and CuS04 5 H20 (6.40 g, 25.62 mmol) was mixed rapidly in 60 mL water, and the resulting yellow solution transferred to a flask containing N- propargyl-di(2-picolyl)amine (6.08 g, 25.62 mmol), prepared as described by Simmons et al., Inorg. Chem., 2013, 52, 5838-5850, dissolved in 60 mL fert-butanol. After rapid stirring, the resulting green solution was transferred to a flask containing tert-butyl 4- azidophenethylcarbamate (5.60 g, 21.35 mmol), prepared according to Murai et al., Eur. J. Org. Chem., 2013, 2428-2433, and allowed to stir for 15 h. The reaction mixture was diluted with ethyl acetate, and washed with 1:1 water/brine. The water phase was then alkalized to pH 9-10 and extracted with ethyl acetate. Combined organic extracts was washed with a 0.025 M EDTA/0.5 M NaHC03 mixture and dried over sodium sulfate. Filtration and subsequent removal of solvent under reduced pressure gave a crude product as a brown oll which could be purified on neutral alumina, gradient 0-1% methanol in dichloromethane, giving the product as a thick orange oll. Purification was performed on three combined batches of different sizes, with a combined yleld of 14.09 g (73%). 1H NMR (400 MHz, DMSO- /6) δ 8.73 (s, 1H), 8.51 (m, 2H), 7.83-7.77 (m, 4H), 7.63 (d, J= 7.9 Hz, 2H), 7.41 (m, 2H), 7.27 (m, 2H), 6.92 (br t, NH, 1H), 3.89 (s, 2H), 3.85 (s, 4H), 3.19 (m, 2H), 2.78 (t, J= 7.3 Hz, 2H), 1.37 (s, 9H). MS (ESI, positive mode) m/z 500.5 [M+H]+. |
Stage #1: N-propargyl-N,N-bis(2-pyridylmethyl)amine With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol Stage #2: tert-butyl 4-azidophenethylcarbamate In water; <i>tert</i>-butyl alcohol for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20 - 100℃; | 36 Example 36 - Synthesis of tert-butyl (4-(2-(4-((bis(pyridin-2-ylmethyl)amino)methyl)- lH-l,2,3-triazol-l-yl)acetamido)phenethyl)carbamate General procedure: Tert-butyl (4-(2-azidoacetamido)phenethyl)carbamate as prepared in Example 1 (1 eq) is suspended in a mixture of fert-butanol and water or another appropriate solvent mixture, and mixed with copper sulfate (0.1-1.0 eq). N,N-bis(pyridin-2-ylmethyl)prop-2-yn-l -amine (1.0- 100 eq) is then added to the stirring mixture and it is stirred for 1-72 hours at a temperature between 20-100°C or until all starting material is consumed as monitored by TLC or HPLC. The reaction mixture is then either diluted with water and extracted with an appropriate organic solvent (e.g. DCM) three times, the combined organic phases dried over K2S04, filtered and concentrated in vacuo or directly purified by column chromatography using an appropriate combination of stationary phase and solvent mixture or recrystallization from an appropriate solvent or solvent mixture to give the titled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / <i>tert</i>-butyl alcohol / 15 h 2: hydrogenchloride / 1,4-dioxane / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol 1.2: 15 h 2.1: hydrogenchloride / 1,4-dioxane / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / <i>tert</i>-butyl alcohol / 15 h 2: hydrogenchloride / 1,4-dioxane / Inert atmosphere 3: HATU; 4-methyl-morpholine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / <i>tert</i>-butyl alcohol / 15 h 2: hydrogenchloride / 1,4-dioxane / Inert atmosphere 3: HATU; 4-methyl-morpholine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Cooling with ice 4: trifluoroacetic acid / water / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In methanol at 20℃; for 3h; Inert atmosphere; | Synthesis of iron(II) complex Fe2L2(l-Cl)2Cl2 The ligand L (474 mg, 2 mmol) was dissolved in degassedmethanol (10 mL) and then the degassed methanolic solution ofFeCl24H2O (397 mg, 2 mmol) was added into the above solution.The mixture was stirred for 3 h under argon atmosphere at roomtemperature to afford yellow solid. The solution was removedunder reduced pressure to collect the yellow solid (550 mg, 76%),which was washed with water (3 30 mL) and diethyl ether(3 30 mL) successively, and then dried in vacuo. Dark yellowcrystals suitable for X-ray analysis were obtained from its solutionin a mixture of diethyl ether-methanol in a few days at room temperature.Elemental analysis calculated for C30H30N6Fe2Cl4: Calc. C,49.49; H, 4.15; N, 11.54; found: C, 49.46; H, 4.10; N, 11.18%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(II) acetate monohydrate; ascorbic acid In tetrahydrofuran; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(II) acetate monohydrate; ascorbic acid In tetrahydrofuran; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51 mg | With piperidine; copper(l) iodide In acetonitrile at 100℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.2% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.6% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40.8% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43.8% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol 1.2: 15 h 2.1: hydrogenchloride / 1,4-dioxane / Inert atmosphere 3.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol 1.2: 15 h 2.1: hydrogenchloride / 1,4-dioxane / Inert atmosphere 3.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 48 h / 0 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 4.5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol 1.2: 15 h 2.1: hydrogenchloride / 1,4-dioxane / Inert atmosphere 3.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; <i>tert</i>-butyl alcohol 1.2: 15 h 2.1: hydrogenchloride / 1,4-dioxane / Inert atmosphere 3.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With copper(II) sulfate; sodium L-ascorbate In water; <i>tert</i>-butyl alcohol for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(actonitrile)copper(I) hexafluorophosphate In 1-methyl-pyrrolidin-2-one; ethanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With tetrakis(actonitrile)copper(I) hexafluorophosphate In 1-methyl-pyrrolidin-2-one; ethanol at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrakis(actonitrile)copper(I) hexafluorophosphate / ethanol; 1-methyl-pyrrolidin-2-one / 24 h / 20 °C / Inert atmosphere 2: dimethyl sulfoxide / pH 7.4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Stage #1: N-propargyl-N,N-bis(2-pyridylmethyl)amine; 6-azido-1H,3H-benzo[de]isochromene-1,3-dione With tetrakis(actonitrile)copper(I) hexafluorophosphate In 1-methyl-pyrrolidin-2-one; ethanol for 24h; Inert atmosphere; Darkness; Stage #2: Propargylamine In 1-methyl-pyrrolidin-2-one; ethanol at 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / ethanol; 1-methyl-pyrrolidin-2-one / 24 h / Inert atmosphere; Darkness 1.2: 16 h / 20 °C / Inert atmosphere 2.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / ethanol; 1-methyl-pyrrolidin-2-one / 24 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / ethanol; 1-methyl-pyrrolidin-2-one / 24 h / Inert atmosphere; Darkness 1.2: 16 h / 20 °C / Inert atmosphere 2.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / ethanol; 1-methyl-pyrrolidin-2-one / 24 h / 20 °C / Inert atmosphere |
[ 51639-58-8 ]
N-(Pyridin-2-ylmethyl)ethanamine
Similarity: 0.90
[ 51639-58-8 ]
N-(Pyridin-2-ylmethyl)ethanamine
Similarity: 0.90