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Usage

Uses

Used in Pharmaceutical Synthesis:
1,2-Ethanediamine, N,N'-dimethyl-N,N'-bis(2-pyridinylmethyl)is used as an intermediate in the synthesis of 8-Hydroxy Efavirenz (H941830), which is a metabolite of Efavirenz (E425000). Efavirenz is a non-nucleoside HIV-1 reverse transcriptase inhibitor, playing a crucial role in the treatment of HIV/AIDS. The compound's ability to form a key intermediate in the synthesis process makes it an essential component in the development of antiretroviral drugs.
Additionally, 1,2-Ethanediamine, N,N'-dimethyl-N,N'-bis(2-pyridinylmethyl)is considered a potential candidate for bioreductively activated prodrugs. These prodrugs are designed to be selectively reduced by biological systems, such as enzymes or cellular reductants, to release the active drug molecule. This approach can improve the drug's pharmacokinetic properties, such as solubility, stability, and bioavailability, as well as reduce side effects and toxicity.

Upstream product

• 4377-33-7 2-chloromethylpyridine 
• 110-70-3 N,N`-dimethylethylenediamine 
• 6959-47-3 2-chloromethylpyridine hydrochloride 
• 50-00-0 formaldehyd 
• 4608-34-8 N,N'-bis(2-pyridylmethyl)ethylenediamine 

Relevant academic research and scientific papers

DFT and experimental studies of perchlorate ion coordination in cis/trans-copper(II) complexes of tetradentate pyridyl ligands

Spectral and structural studies of N,N′-dimethyl-N,N′-bis- (pyridin-2-ylmethyl)-1,2-diaminoethane (L1), N,N′-dimethyl-N,N′- bis(pyridin-2-ylmethyl)-1,3-diaminopropane (L2), and their copper(II) complexes were carried out by spectroscopic and DFT methods. The DFT results show that conventional and nonconventional H-bonds present in L1 and L2 influence the NMR chemical shifts at different pH values, which thus suggests that the protonation sites at the pyridyl and tertiary nitrogen atoms of the ligands change the chemical environment of the adjacent carbon atoms; this observation is consistent with 13C NMR spectra recorded at different pH values. Furthermore, for their copper complexes, two possible geometrical isomers (cis and trans) are obtained; for example, cis-[CuL 1]2+, where both NCH3 groups are oriented in the same plane, is in equilibrium with its trans isomer and, as a result, a small energy difference (0.9 kcal mol-1) appears. In contrast, trans-[CuL2]2+ does not equilibrate with the cis isomer, because there is a greater energy difference (ΔE = 3.9 kcal mol -1) between the two isomers. Indeed, when [CuL1] 2+ with two perchlorate ions was optimized, it was found that although only cis-[CuL1]2+ was able to accommodate a perchlorate ion in the axial position of the square pyramidal geometry by stabilizing the structure with two cis NCH3 groups through H-bonds, the trans isomer was unable to retain the perchlorate ion in the coordination sphere, because the NCH3 groups were in the trans position; this disfavors the presence of the perchlorate ion in the sphere, because of the absence of H-bonds. This is consistent with the X-ray structure, in which cis-[CuL1(ClO4)]+ is resolved, whereas the trans isomer is not. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Selectivity Trends in Olefin Epoxidations Catalyzed by (NNNN)Manganese(+II) Complexes using Trifluoroethanol as the Solvent

The epoxidation of olefins is certainly one of the most important oxygen-transfer reactions in organic synthesis. The development of both regio- and stereoselective protocols and the search for catalysts that combine high selectivity with abundancy is a topic of current interest. Herein, we report an unexpected odd–even-type selectivity trend in the diastereoselective epoxidation of unfunctionalized aliphatic alkenes by using a non-hem-type Mn catalyst in trifluoroethanol as the solvent.

Copper(II)-azido complexes constructed from polypyridyl amine ligands

A novel 1-D polymer Cu(II) complex bridged by perchlorate ions and azide ligand with the structural formula [Cu(DPA)(N3)(μO,O-ClO 4)]n (1), {[Cu(Ldpdmen)(μ1,3-N 3)]ClO4}n (2), {[Cu2(μ-L py)(μ-1,1,3-N3)(μ-1,3-N3)](ClO 4)2}n (3) and {[Cu2(L T)(μ2-1,3-N3)(N3)(H 2O)](ClO4)2H2O}n (4) where DPA = di(2-pyridylmethyl)amine, Ldpdmen = N,N′-bis(2- pyridylmethyl)-N,N′-dimethylethylenediamine and Lpy = 2,6-bis[bis(2-pyridylmethyl)aminomethyl]pyridine and LT = 3,5-bis[bis(2-pyridylmethyl) aminomethyl]toluene were synthesized. The complexes were characterized by spectroscopic techniques (IR and visible) and by single crystal X-ray crystallography. The magnetic properties were also measured for 1-3 at variable temperatures (4.5-300 K). Compound 1 has the copper center in a 4+2 geometry with the equatorial plane formed through the three N-donors of the DPA and an azido group which acting as a monodentate ligand. The 1-D chain is generated via the axial O,O′-bridging perchlorato groups where the intra-chain Cua??Cu distance is 6.9416(16) A?. In complex 2, the Cu center is ligated by the four N-donor atoms of Ldpdmen amine ligand and two N atoms of the EE bridging azido groups in a cis-coordinated asymmetric EE bonding fashion. The intra-chain Cua??Cu distance in this complex is 5.7949(15) A?.

Mononuclear nickel (II) and copper (II) coordination complexes supported by bispicen ligand derivatives: Experimental and computational studies

The synthesis, characterization and density functional theory calculations of mononuclear Ni and Cu complexes supported by the N,N′-dimethyl-N,N′-bis-(pyridine-2-ylmethyl)-1,2-diaminoethane ligand and its derivatives are reported. The complexes were characterized by X-ray crystallography as well as by UV?visible absorption spectroscopy and EPR spectroscopy. The solid state structure of these coordination complexes revealed that the geometry of the complex depended on the identity of the metal center. Solution phase characterization data are in accord with the solid phase structure, indicating minimal structural changes in solution. Optical spectroscopy revealed that all of the complexes exhibit color owing to d-d transition bands in the visible region. Magnetic parameters obtained from EPR spectroscopy together with other structural data suggest that the Ni(II) complexes are in a pseudo-octahedral geometry and Cu(II) complexes are in a distorted square pyramidal geometry. In order to understand in detail how ligand sterics and electronics affect complex topology detailed computational studies were performed. The series of complexes reported in this article will add significant value in the field of coordination chemistry as Ni(II) and Cu(II) complexes supported by tetradentate pyridyl based ligands are rather scarce.

Copper tetradentate N2Py2 complexes with pendant bases in the secondary coordination sphere: Improved ligand synthesis and protonation studies

An improved preparation for a tetradentate neutral N2Py2 ligand with two dimethylamine functionalities in the secondary coordination sphere (LDMA) is reported. This synthetic route uses cheaper and more readily available p

Synthesis of water-soluble Ni(II) complexes and their role in photo-induced electron transfer with MPA-CdTe quantum dots

Abstract: Photocatalytic water splitting using solar energy for hydrogen production offers a promising alternative form of storable and clean energy for the future. To design an artificial photosynthesis system that is cost-effective and scalable, earth a

Electrochemical Exploration of Active Cu-Based Atom Transfer Radical Polymerization Catalysis through Ligand Modification

The intersection between Cu-catalyzed atom transfer radical polymerization (ATRP) and organometallic mediated radical polymerization (OMRP) has been recently shown to be a result of competition between the CuI and CuII complexes of polyamine ligands for the same organic free radical. The tetradentate ligands N,N′-bis-2′-pyridylmethyl-ethane-1,2-diamine (L1) and N,N′-dimethyl-N,N′-bis-2′-pyridylmethyl-ethane-1,2-diamine (L2) form stable Cu complexes which, depending on their oxidation state, can either liberate or complex organic radicals. Herein, we show that this process may be affected by subtle changes to the ligand system. Switching from a tertiary amine (L2) to a secondary amine (L1) retains ATRP and OMRP activity through a series of cyclic voltammetry measurements in the presence of the initiator bromoacetonitrile.

Effects of denticity and ligand rigidity on reactivity of copper complexes with cumyl hydroperoxide

Cu(II) complexes bearing N2/Py2 tetradentate ligands consisting of two pyridyl arms and a flexible ethyldiamine backbone, [(BPMEN)Cu(ClO4)2] (1), with rigid cyclohexyl backbone [(BPMCN)Cu(ClO4)2] (2), and substituted with bispyrrolidyl [(PDP)Cu(ClO4)2] (3), and Cu(II) complex bearing N2/Py3 pentadentate ligand, [(TPMEN)Cu(ClO4)2] (4), were synthesized and structurally characterized. Reactivity of 1–4 with cumyl hydroperoxide was investigated to study the effects of ligand rigidity and denticity on the mechanism of O–O bond cleavage. Results presented herein illustrate that 1–3 favors homolysis, however 4 showed little to almost no impact on O–O bond cleavage.

O-H and (CO)N-H bond weakening by coordination to Fe(ii)

New N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-ethane-1,2-diamine derivatives bearing covalently linked OH and (CO)NH groups have been synthesized. The coordination of those pendant hydroxyl/amide groups to a Fe(ii) metal center is demonstrated both in solution, even in the presence of chloride as the counterion, and in solid state, by means of X-ray diffraction crystal structures. As a result of this coordination, the experimental bond dissociation free energies (BDFE) of O-H and (CO)N-H bonds are remarkably diminished down to 76.0 and 80.5 kcal mol-1 respectively, which is also in agreement with DFT-based theoretical calculations. These BDFE values are in the range of commonly used hydrogen-atom donor reagents. The strategy presented here allows an unequivocal evaluation of the influence of metal coordination in X-H bond weakening in organic solvents which could be easily extended to other metal centers.

Reactivity of bio-inspired Cu(II) (N2/Py2) complexes with peroxide at room temperature

Developing coordination complexes of earth abundant metals that can perform substrate oxidations under benign conditions is an ongoing challenge. Herein, the reactivity of two mononuclear Cu-complexes toward the oxidant H2O2 is reported. Both complexes displayed ligand oxidation upon reaction with the oxidant. Analysis of spectroscopic data established that the respective product complexes contained mononuclear Cu(II) centers. Moreover, treatment of these Cu-complexes with oxidant in the presence of substrate resulted in the interception of ligand oxidation with preferential oxidation of the substrate. Computational studies identified plausible mechanistic pathways, suggesting a copper-oxyl intermediate as the likely reactive intermediate responsible for substrate and ligand oxidation. To our knowledge, this is the first Cu-mediated system that showed ligand oxidation, oxo-transfer capability, and external hydrocarbon oxidation under stoichiometric conditions.