Month: January 2023

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide – Functional Groups Tolerance, Scope, and Limitations was written by Popov, Kirill K.;Campbell, Joanna L. P.;Kysilka, Ondrej;Hosek, Jan;Davies, Christopher D.;Pour, Milan;Kocovsky, Pavel. And the article was included in Journal of Organic Chemistry in 2022.Related Products of 10282-32-3 This article mentions the following:

Aldimines R¹CH₂NHR² (R¹ = but-3-yn-1-yl, Ph, thiophen-2-yl, etc.; R² = Bu, Bn, cyclohexyl, 5-methyl-1,3,4-thiadiazol-2-yl, etc.), generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes R¹CHO and aliphatic, aromatic, and heteroaromatic primary or secondary amines R²NH₂, can be reduced with trichlorosilane in the presence of DMF (DMF) as an organocatalyst (≤10 mol%) in toluene or CH₂Cl₂ at room temperature The reduction tolerates ketone carbonyls, esters, amides, nitriles, sulfones, sulfonamides, NO₂, SF₅, and CF₃ groups, boronic esters, azides, phosphine oxides, C=C and CC bonds, and ferrocenyl nucleus but sulfoxides and N-oxides are reduced. α,β-Unsaturated aldimines undergo 1,2-reduction only, leaving the C=C bond intact. N-Monoalkylation of primary amines is attained with a 1:1 aldehyde to amine ratio, whereas excess of the aldehyde (≥2:1) allows second alkylation, giving rise to tertiary amines. Reductive N-alkylation of α-amino acids proceeds without racemization; the resulting products, containing a CC bond or N₃ group, are suitable for click chem. This reaction thus offers advantages over the traditional methods (borohydride reduction or catalytic hydrogenation) in terms of efficiency and chemoselectivity. Solubility of some of the reacting partners appears to be the only limitation. The byproducts generated by the workup with aqueous NaHCO₃ (i.e., NaCl and silica) are environmentally benign. As a greener alternative, DMA can be employed as a catalyst instead of DMF. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Related Products of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

“Water Strider” Legs with a Self-Assembled Coating of Single-Crystalline Nanowires of an Organic Semiconductor was written by Jiang, Lang;Yao, Xi;Li, Hongxiang;Fu, Yanyan;Chen, Li;Meng, Qing;Hu, Wenping;Jiang, Lei. And the article was included in Advanced Materials (Weinheim, Germany) in 2010.Synthetic Route of C18H10N2 This article mentions the following:

Superhydrophobic surfaces are reported composed of crystalline nanowires of an organic semiconductor. Model copper waterstriders weighing 259.6 mg with self-assembled crystalline nanowires on their legs can easily stand on the surface of water. 1.0 Mg of such organic crystalline nanowires assembled on the legs could maximum float a 372 mg model strider. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Synthetic Route of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure-Activity Relationships, and Sleep-Promoting Properties in Rats was written by Brotschi, Christine;Roch, Catherine;Gatfield, John;Treiber, Alexander;Williams, Jodi T.;Sifferlen, Thierry;Heidmann, Bibia;Jenck, Francois;Bolli, Martin H.;Boss, Christoph. And the article was included in ChemMedChem in 2019.Name: 2-(Trifluoromethoxy)benzonitrile This article mentions the following:

The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzoxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3, I), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chem. instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51, II), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4Name: 2-(Trifluoromethoxy)benzonitrile).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Name: 2-(Trifluoromethoxy)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Amination of Alcohols Catalyzed by Copper-Aluminum Hydrotalcite: A Green Synthesis of Amines was written by Likhar, Pravin R.;Arundhathi, Racha;Kantam, Mannepalli Lakshmi;Prathima, Parvathaneni Sai. And the article was included in European Journal of Organic Chemistry in 2009.Safety of 4-(Benzylamino)benzonitrile This article mentions the following:

Copper-aluminum hydrotalcite (CuAl-HT)/K₂CO₃ has been employed in the activation of various benzyl alcs. with benzylamines to afford the corresponding amines in good to high yields. Experimentation showed that the reaction takes place through sequential transformations: the oxidation of alcs. into carbonyl compounds, imine formation between amines and carbonyl compounds, and then reduction of imines to amines, heterogeneously catalyzed by non-noble Cu-Al HT catalyst in a one-pot and straightforward fashion. The process was further extended to amination of alcs. with anilines which are often resistant to alkylation reactions when substituted with strong electron-withdrawing groups. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Safety of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Safety of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-Activity Relationship Exploration of NNIBP Tolerant Region I Leads to Potent HIV-1 NNRTIs was written by Kang, Dongwei;Sun, Yanying;Murugan, N. Arul;Feng, Da;Wei, Fenju;Li, Jing;Jiang, Xiangyi;De Clercq, Erik;Pannecouque, Christophe;Zhan, Peng;Liu, Xinyong. And the article was included in ACS Infectious Diseases in 2020.Related Products of 1753-48-6 This article mentions the following:

Previous efforts in our lab have led to the development of human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse transcriptase inhibitor (NNRTI) thiophene[3,2-d]pyrimidine compound 1 (K-5a2) with promising activity against wild-type and mutant HIV-1 strains. In this work, a series of novel diarylpyrimidines derivatives carrying a structurally diverse motif at the right wing of the lead K-5a2 was designed and synthesized as potential anti-HIV-1 agents. The results demonstrated that 8a yielded exceptionally potent activity against HIV-1 wild-type (50% effective concentration (EC₅₀) = 3.30 nM) and mutant strain RES056 (EC₅₀ = 22.6 nM) in MT-4 cells; in the reverse transcriptase inhibitory assay, 8a (half maximal inhibitory concentration (IC₅₀) = 0.028μM) was remarkably superior to that of K-5a2 (IC₅₀ = 0.300μM) and comparable to that of etravirine (ETR; IC₅₀ = 0.011μM). Notably, 8a exhibited better druggability than that of K-5a2, including significantly reduced CYP enzymic inhibitory activity (IC₅₀ > 50μM), lower human ether-á-go-go related gene (hERG) inhibition (IC₅₀ > 30μM), and improved metabolic stability (short half-life, T_1/2 = 77.5 min) in vitro. In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Related Products of 1753-48-6).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Related Products of 1753-48-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, Synthesis, and Molecular-modeling Study of Aminothienopyridine Analogues of Tacrine for Alzheimer’s Disease was written by Badran, Mohga M.;Abdel Hakeem, Maha;Abuel-Maaty, Suzan M.;El-Malah, Afaf;Abdel Salam, Rania M.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2010.Reference of 70291-62-2 This article mentions the following:

2-Amino-3-cyanothiophenes were successfully condensed with a number of cycloalkanones to afford tacrine analogs in a one-step reaction mediated with Lewis acid. The newly synthesized compounds have been tested for their ability to inhibit acetylcholine esterase (AChE) activity using tacrine as standard drug. Some of the tested compounds showed moderate inhibitory activity in comparison with tacrine, especially compounds 6a (I) which displayed the highest inhibitory activity. Furthermore, mol.-modeling studies were performed in order to rationalize the obtained biol. results. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Reference of 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Reference of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Preparation of Tertiary Benzylic Nitriles from Aryl Fluorides was written by Caron, Stephane;Vazquez, Enrique;Wojcik, Jill M.. And the article was included in Journal of the American Chemical Society in 2000.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

An efficient method for the addition of secondary nitriles to fluoroarenes was described. The reaction is specific to hexamethyldisilazane potassium salt, but proceeds with a variety of substrates. For example, the reaction of 1-fluoro-2-methoxybenzene with 2-methylpropanenitrile in the presence of hexamethyldisilazane potassium salt in toluene or THF gave 2-methoxy-α,α-dimethylbenzeneacetonitrile. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Safety of 2-(4-Methoxyphenyl)-2-methylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Stereoselective synthesis of spirocyclohexadiene-pyrazolones via organic base and/or hydrogen bonding assisted [3+3] annulation reactions was written by Sun, Bing-Bing;Zhang, Jun-Qi;Chen, Jun-Bo;Fan, Wei-Tai;Yu, Jie-Qiang;Hu, Jia-Ming;Wang, Xing-Wang. And the article was included in Organic Chemistry Frontiers in 2019.SDS of cas: 55490-87-4 This article mentions the following:

The 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3+3] cycloaddition reaction of α-arylidene pyrazolinones I (R¹ = Ph, 3-fluorophenyl, 2-naphthyl, 2-thienyl, etc.; R² = Ph, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl; R³ = Ph, 3-chlorophenyl, 4-cyanophenyl, 4-methylphenyl, 4-methoxyphenyl) and 2-benzylidenemalononitriles R⁴CH=C(CN)₂ (R² = Ph, 2-chlorophenyl, 9-anthracenyl, etc.) under mild reaction conditions has been reported, which afforded the spirocyclohexadiene-pyrazolones II in good yields with moderate to good diastereoselectivities. By the use of a cinchona alkaloid derived bifunctional squaramide-tertiary amine catalyst, an asym. variant of this [3 + 3] cycloaddition reaction has also been developed to provide optically active spirocyclohexadiene-pyrazolones bearing an all-carbon quaternary chiral center III in good yields with excellent enantioselectivities and moderate diastereoselectivities. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4SDS of cas: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.SDS of cas: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Second harmonic generation from the single crystals of N-substituted 4-cyanoanilines was written by Hashimoto, H.;Okada, Y.;Okamoto, N.;Matsushima, R.. And the article was included in Journal of Luminescence in 2000.Category: nitriles-buliding-blocks This article mentions the following:

Six N-substituted derivatives of 4-cyanoaniline (pCA) were synthesized and their phys. and optical properties were examined in the search for 2nd-order nonlinear optical materials with enough crystal dimensions together with blue-light transparency. Among the derivatives examined, N-diphenylmethyl-pCA and N-2-naphthylmethyl-pCA afforded single crystals that lack a center of symmetry. Although the 2nd harmonic (SH) activities of these derivatives were not enough for the practical purposes, their cut-off wavelengths were shorter than 330 nm and showed sufficient blue-light transparency. Quant. prediction of the SH activity was also attempted. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Category: nitriles-buliding-blocks).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

INCB050465 (Parsaclisib), a Novel Next-Generation Inhibitor of Phosphoinositide 3-Kinase Delta (PI3Kδ) was written by Yue, Eddy W.;Li, Yun-Long;Douty, Brent;He, Chunhong;Mei, Song;Wayland, Brian;Maduskuie, Thomas;Falahatpisheh, Nikoo;Sparks, Richard B.;Polam, Padmaja;Zhu, Wenyu;Glenn, Joseph;Feng, Hao;Zhang, Ke;Li, Yanlong;He, Xin;Katiyar, Kamna;Covington, Maryanne;Feldman, Patricia;Shin, Niu;Wang, Kathy He;Diamond, Sharon;Li, Yu;Koblish, Holly K.;Hall, Leslie;Scherle, Peggy;Yeleswaram, Swamy;Xue, Chu-Biao;Metcalf, Brian;Combs, Andrew P.;Yao, Wenqing. And the article was included in ACS Medicinal Chemistry Letters in 2019.Recommanded Product: 60025-09-4 This article mentions the following:

A medicinal chem. effort focused on identifying a structurally diverse candidate for phosphoinositide 3-kinase delta (PI3Kδ) led to the discovery of clin. candidate INCB050465 (20, parsaclisib). The unique structure of 20 contains a pyrazolopyrimidine hinge-binder in place of a purine motif that is present in other PI3Kδ inhibitors, such as idelalisib (1), duvelisib (2), and INCB040093 (3, dezapelisib). Parsaclisib (20) is a potent and highly selective inhibitor of PI3Kδ with drug-like ADME properties that exhibited an excellent in vivo profile as demonstrated through pharmacokinetic studies in rats, dogs, and monkeys and through pharmacodynamic and efficacy studies in a mouse Pfeiffer xenograft model. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Recommanded Product: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts