Category: 530-40-5

Alessi, Manlio published the artcileDirected ortho Metalation-Boronation and Suzuki-Miyaura Cross Coupling of Pyridine Derivatives: A One-Pot Protocol to Substituted Azabiaryls, HPLC of Formula: 530-40-5, the publication is Journal of Organic Chemistry (2007), 72(5), 1588-1594, database is CAplus and MEDLINE.

A general method for the regioselective synthesis of aryl-substituted pyridines by a one-pot procedure involving a Directed ortho-metalation-boronation-Suzuki-Miyaura cross-coupling sequence is described. Aside from the three isomeric pyridinecarboxamides, chloro-, fluoro-, and O-carbamoyl pyridines are adapted to this method providing a range of disubstituted pyridines. The one-pot procedure allows to avoid the recognized difficult isolation of pyridylboronic acids and their instability toward deboronation. The efficient synthesis of 5-(un)substituted N,N-diethyl-3-hydroxy-2-pyridinecarboxamides by a one-pot metalation-boronation-oxidation sequence using LDA-B(OCHMe₂)₃ and avoiding self-condensation of incipient ortho-metalated species is also described. Some of aryl-substituted pyridinecarboxamides were converted into azafluorenones by a directed remote metalation protocol. A comprehensive survey of pyridylboronates, which are of considerable interest in contemporary heterocyclic synthetic chem., is also provided.

Journal of Organic Chemistry published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, HPLC of Formula: 530-40-5.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Mikhailova, T. A. published the artcilePolarographic study of some nitrogen-containing heterocycles, COA of Formula: C10H14N2O, the publication is Zhurnal Obshchei Khimii (1969), 39(1), 26-30, database is CAplus.

Polarographic halfwave potentials were reported in the pH range of 1.85-11.6 for pyridine, quinoline, acridine, their 4-carboxylic acids, and the amides of these acids with N-CHMeCH2Ph grouping. Also included were data on N-(1-methyl-2-phenylethyl)amides of isonicotinic acid with the following 2,6-ring substituents: H, H; Cl, Cl; MeO, MeO; Et2N, Et2N; Cl, MeO; Cl, Et2N. N,N-diethylisonicotinamide with the following 2,6-substituents were also reported: H, H; Cl, Cl; Cl, MeO; MeO, MeO; Cl, Et2N; Et2N, Et2N. The main center of reaction in these compounds is the C:N link which gives the 1st polarographic wave at any pH value. Introduction of 4-substituents with electron-acceptor properties serves to lower the halfwave potential; introduction of electron donor groups in 2,6-positions raises the halfwave potential. The CO2H and CONHR groups cause a 2nd polarographic wave in neutral medium only. Treating the acyl chloride with Et2NH in C6H6 gave the diethylamides of: isonicotinic acid, b3 133°, n20D 1.5238; 2,6-dichloroiso-nicotinic acid (I), m. 82-4°; 2-chloro-6-methoxy analog, b3 153°; and the 2,6-dimethoxy analog, m. 87-8°. Heating the diethylamide of I with Et2NH at 100° 1 day gave the diethylamide of 2-chloro-6-diethylaminoisonicotinic acid, b4 182-4°; similarly, by heating 26 hrs. at 200°, the 2,6-bis(diethylamino)analog, m. 54-6°, b3 185-7°, was prepared

Zhurnal Obshchei Khimii published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, COA of Formula: C10H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Jo, Woohyun published the artcileTransition-Metal-Free Regioselective Alkylation of Pyridine N-Oxides Using 1,1-Diborylalkanes as Alkylating Reagents, Formula: C10H14N2O, the publication is Angewandte Chemie, International Edition (2016), 55(33), 9690-9694, database is CAplus and MEDLINE.

Reported herein is an unprecedented base-promoted deborylative alkylation of pyridine N-oxides using 1,1-diborylalkanes as alkyl sources. The reaction proceeds efficiently for a wide range of pyridine N-oxides and 1,1-diborylalkanes with excellent regioselectivity. The utility of the developed method is demonstrated by the sequential C-H arylation and methylation of pyridine N-oxides. The reaction also can be applied to the direct introduction of a Me group to 9-O-methylquinine N-oxide; thus it can serve as a powerful method for late-stage functionalization.

Angewandte Chemie, International Edition published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Formula: C10H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Yakovleva, N. L. published the artcileReaction of carboxy-, carbethoxy-, and hydroxymethylpyridines with phosphorous amides, Safety of N,N-Diethylisonicotinamide, the publication is Khimiko-Farmatsevticheskii Zhurnal (1980), 14(1), 67-9, database is CAplus.

Heating nicotinic acid, isonicotinic acid or their Et esters with P(NEt₂)₃ gave 34.8-88% resp. diethylamides; yields were higher (88%, 79.5%) using the acids. Amines I and II were prepared in 21.5 and 14.8% yield resp. from the corresponding hydroxymethyl derivatives

Khimiko-Farmatsevticheskii Zhurnal published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H9NO, Safety of N,N-Diethylisonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Collins, Scott published the artcileAdditions of alkyllathanum triflates to carbonyl compounds: reactive organometallic nucleophiles, Name: N,N-Diethylisonicotinamide, the publication is Journal of Organic Chemistry (1990), 55(11), 3565-8, database is CAplus.

Addition of alkyl- or aryllithium compounds to lanthanum(III) triflate in ethereal solvents produces the title reagents RLa(O₃SCF₃)₂ (R = Me, Bu, Ph) that undergo nucleophilic addition to carbonyl compounds under mild conditions. These reagents resemble alkylcerium halides in their reactions with enolizable carbonyl compounds but are more reactive. In particular, they are useful for the conversion of hindered, tertiary amides to ketones. ¹H NMR spectroscopy was employed to clarify mechanistic aspects of this addition process. The title reagents actually appear to be a mixture of several species; formulation of their structure has proven elusive. However, in the presence of a tertiary amide, these species react to give a single, tetrahedral intermediate, which is quite stable in solution

Journal of Organic Chemistry published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Name: N,N-Diethylisonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Fier, Patrick S. published the artcileSelective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction, Name: N,N-Diethylisonicotinamide, the publication is Science (Washington, DC, United States) (2013), 342(6161), 956-960, database is CAplus and MEDLINE.

Fluorinated heterocycles are prevalent in pharmaceuticals, agrochems., and materials. However, reactions that incorporate fluorine into heteroarenes are limited in scope and can be hazardous. The authors present a broadly applicable and safe method for the site-selective fluorination of a single carbon-hydrogen bond in pyridines and diazines using com. available silver(II) fluoride. The reactions occur at ambient temperature within 1 h with exclusive selectivity for fluorination adjacent to nitrogen. The mild conditions allow access to fluorinated derivatives of medicinally important compounds, as well as a range of 2-substituted pyridines prepared by subsequent nucleophilic displacement of fluoride. Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.

Science (Washington, DC, United States) published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Name: N,N-Diethylisonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Song, Guoyong published the artcileSynthesis of Quinolines via Rh(III)-Catalyzed Oxidative Annulation of Pyridines, Formula: C10H14N2O, the publication is Journal of Organic Chemistry (2011), 76(18), 7583-7589, database is CAplus and MEDLINE.

Selective synthesis of quinolines, e.g., I (R¹ = H, Me, MeO, Cl; R² = H, Me, MeO, Cl), has been achieved via oxidative annulation of functionalized pyridines with two alkyne mols. under Rh(III)-catalyzed cascade C-H activation of pyridines using Cu(OAc)₂ as an oxidant. The selectivity of this reaction is oxidant-dependent, particularly on the anion of the oxidant.

Journal of Organic Chemistry published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C8H7NaO4S, Formula: C10H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Ciusa, W. published the artcileThe ultraviolet spectra of the m- and p-substituted N-alkyl derivatives of pyridine, Recommanded Product: N,N-Diethylisonicotinamide, the publication is Bollettino Scientifico della Facolta di Chimica Industriale di Bologna (1959), 12-26, database is CAplus.

cf. CA 53, 5398e; 53, 20059d. Pyridine derivatives, prepared as described in earlier publications, were dissolved in 0.1N NaCl (pH 6-7), 0.1N HCl (pH 1.1), and in 0.1N NaOH (pH 13.0) to give 0.1-0.05M solutions and their ultraviolet spectra obtained for the range 210-460 mμ at 20 ± 2°. These were presented in 37 absorption curves. The λ_maximum and the extinction (ε × 10^-3) at this wave length in HCl, NaCl, and NaOH for these compounds were: pyridine, 256, 5.4, 3.4, 2.5; methylpyridinium (I) iodide, 260, 4.5, 4.4, 4.8; I bromide, 258, 4.5, 4.5 4.5; I chloride, 258, 4.7, 5.0, 4.9; dodecylpyridinium bromide, 260, 4.0, 3.5, 4.1; myristylpyridinium bromide, 260, 4.5, 4.1, 4.6; cetylpyridinium (II) bromide, 260, 3.4, 3.1, 3.5; II chloride, 260, 4.8, 4.6, 4.8; octadecylpyridinium bromide, 260, 4.9, 3.5, 4.0; Et ester of nicotinic acid (III), 260 (265, 262), 5.0, 2.7, 3.0; III MeI salt, 265, 4.5, 3.9, 4.0; III MeBr salt, 265, 4.5, 4.3, 4.0; III MeCl salt, 265, 4.2, 4.3, 3.4; III BuBr salt, 265, 4.2, 4.3, 3.4; III iso-AmBr salt, 265, 4.5, 4.3, 4.3; nicotinic acid (IV), 261 (262, 264), 4.9, 3.6, 2.8; IV MeI salt, 265, 4.3, 4.9, 4.0; trigonelline, 265, 4.0, 3.8, 4.0; IV amide, 260, 4.8, 3.3, 3.0; IV amide-MeI, 265, 4.9, 4.6, 4.8; IV monomethylamide, 262, 5.7, 3.6, 3.5; IV diethylamide (V), 262, 5.2, 3.6, 3.3; V MeCl salt, 268, 4.3, 4.8, 4.6; V EtCl salt, 268, 4.0, 3.8, 3.8; V iso-PrCl salt, 268, 3.5, 3.5, 3.8; V AmCl salt, 265, 4.0, 3.8, 3.0; V AcCl salt, 268, 4.0, 3.8, 3.6; Et ester of isonicotinic acid (VI), 272 (272, 265), 4.5, 2.8, 2.8; VI MeI salt, 275 (278, 268), 4.5, 4.6, 4.4; VI EtBr salt, 275 (268, 265), 4.1, 3.5, 4.1; VI decyl bromide, 275 (278, 265), 4.3, 3.9, 3.5; isonicotinic acid (VII), 270 (263, 265), 4.1, 3.2, 2.1; isotrigonelline, 272 (265, 265), 3.9, 3.9, 4.1; VII amide, 262 (266, 266), 5.0, 2.8, 2.6; VII amide-MeI, 268 (266, 264), 4.7, 4.8, 4.5; VII diethylamide (VIII), 259 (259, 258), 6.3, 3.3, 3.2; VIII MeCl salt, 262, 5.9, 5.9, 5.7; VIII EtCl salt, 262, 5.8, 5.8, 5.5; VIII cetyl chloride, 262, 6.1, 6.3, 5.7. The lack of influence by CO₂H or CO₂R groups was in disagreement with findings by Black (CA 49, 15389h).

Bollettino Scientifico della Facolta di Chimica Industriale di Bologna published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Recommanded Product: N,N-Diethylisonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Neta, Pedatsur published the artcileUnexpected peaks in tandem mass spectra due to reaction of product ions with residual water in mass spectrometer collision cells, Product Details of C10H14N2O, the publication is Rapid Communications in Mass Spectrometry (2014), 28(23), 2645-2660, database is CAplus and MEDLINE.

Certain product ions in electrospray ionization tandem mass spectrometry react with residual water in the collision cell. This reaction often gives ions that cannot be formed directly from the precursor ions, and this complicates the mass spectra and may distort MRM (multiple reaction monitoring) results. Various drugs, pesticides, metabolites, and other compounds were dissolved in acetonitrile/water/formic acid and studied by electrospray ionization mass spectrometry to record their MS² and MSⁿ spectra in several mass spectrometers (QqQ, QTOF, IT, and Orbitrap HCD). Certain product ions react with residual water in collision cells. The reaction was confirmed by MSⁿ studies and the rate of reaction was determined in the IT instrument using zero collision energy and variable activation times. Examples of product ions reacting with water include Ph and certain substituted Ph cations, benzoyl-type cations formed from protonated folic acid and similar compounds by loss of the glutamate moiety, product ions formed from protonated cyclic siloxanes by loss of methane, product ions formed from organic phosphates, and certain neg. ions. The reactions of product ions with residual water varied greatly in their rate constant and in the extent of reaction (due to isomerization). Thus, various types of product ions react with residual water in mass spectrometer collision cells. As a result, tandem mass spectra may contain unexplained peaks and MRM results may be distorted by the occurrence of such reactions. These often unavoidable reactions must be taken into account when annotating peaks in tandem mass spectra and when interpreting MRM results.

Rapid Communications in Mass Spectrometry published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Product Details of C10H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Wu, Danchen published the artcileIdentification of novel dynamin-related protein 1 (Drp1) GTPase inhibitors: Therapeutic potential of Drpitor1 and Drpitor1a in cancer and cardiac ischemia-reperfusion injury, Computed Properties of 530-40-5, the publication is FASEB Journal (2020), 34(1), 1447-1464, database is CAplus and MEDLINE.

Mitochondrial fission is important in physiol. processes, including coordination of mitochondrial and nuclear division during mitosis, and pathol. processes, such as the production of reactive oxygen species (ROS) during cardiac ischemia-reperfusion injury (IR). Mitochondrial fission is mainly mediated by dynamin-related protein 1 (Drp1), a large GTPase. The GTPase activity of Drp1 is essential for its fissogenic activity. Therefore, we aimed to identify Drp1 inhibitors and evaluate their anti-neoplastic and cardioprotective properties in five cancer cell lines (A549, SK-MES-1, SK-LU-1, SW 900, and MCF7) and an exptl. cardiac IR injury model. Virtual screening of a chem. library revealed 17 compounds with high predicted affinity to the GTPase domain of Drp1. In silico screening identified an ellipticine compound, Drpitor1, as a putative, potent Drp1 inhibitor. We also synthesized a congener of Drpitor1 to remove the methoxymethyl group and reduce hydrolytic lability (Drpitor1a). Drpitor1 and Drpitor1a inhibited the GTPase activity of Drp1 without inhibiting the GTPase of dynamin 1. Drpitor1 and Drpitor1a have greater potency than the current standard Drp1 GTPase inhibitor, mdivi-1, (IC50 for mitochondrial fragmentation are 0.09, 0.06, and 10μM, resp.). Both Drpitors reduced proliferation and induced apoptosis in cancer cells. Drpitor1a suppressed lung cancer tumor growth in a mouse xenograft model. Drpitor1a also inhibited mitochondrial ROS production, prevented mitochondrial fission, and improved right ventricular diastolic dysfunction during IR injury. In conclusion, Drpitors are useful tools for understanding mitochondrial dynamics and have therapeutic potential in treating cancer and cardiac IR injury.

FASEB Journal published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H15ClO3S, Computed Properties of 530-40-5.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics