Author: Jessica.F

In 2018,Thota, Ganesh Kumar; Sun, Gui-Jun; Deng, Tao; Li, Yi; Kang, Qiang published 《Enantioselective Conjugate Addition of 2-Acylimidazoles with Nitroalkenes Promoted by Chiral-at-Metal Rhodium(III) Complexes》.Advanced Synthesis & Catalysis published the findings.Formula: C4H9NO2 The information in the text is summarized as follows:

An enantioselective conjugate addition of 2-acylimidazoles with nitroalkenes catalyzed by chiral-at-metal rhodium(III) complex under mild reaction conditions was developed, affording versatile γ-nitro ketone skeletons in good yields with excellent enantioselectivities (up to >99% ee).N-Methoxy-N-methylacetamide(cas: 78191-00-1Formula: C4H9NO2) was used in this study.

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Formula: C4H9NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In 2019,Chemistry – A European Journal included an article by van Leest, Nicolaas P.; Grooten, Lars; van der Vlugt, Jarl Ivar; de Bruin, Bas. Category: amides-buliding-blocks. The article was titled 《Uncatalyzed Oxidative C-H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study》. The information in the text is summarized as follows:

A new method for the one-step C-H amination of xanthene and thioxanthene with sulfonamides is reported, without the need for any metal catalyst. A benzoquinone was employed as a hydride (or two-electron and one-proton) acceptor. Moreover, a previously unknown and uncatalyzed reaction between iminoiodanes and xanthene, thioxanthene and dihydroacridines (9,10-dihydro-9-heteroanthracenes or dihydroheteroanthracenes) is disclosed. The reactions proceed through hydride transfer from the heteroarene substrate to the iminoiodane or benzoquinone, followed by conjugate addition of the sulfonamide to the oxidized heteroaromatic compounds These findings may have important mechanistic implications for metal-catalyzed C-H amination processes involving nitrene transfer from iminoiodanes to dihydroheteroanthracenes. Due to the weak C-H bond, xanthene is an often-employed substrate in mechanistic studies of C-H amination reactions, which are generally proposed to proceed via metal-catalyzed nitrene insertion, especially for reactions involving nitrene or imido complexes that are less reactive (i.e., less strongly oxidizing). However, these substrates clearly undergo non-catalyzed (proton-coupled) redox coupling with amines, thus providing alternative pathways to the widely assumed metal-catalyzed pathways. In the experiment, the researchers used 4-Methylbenzenesulfonamide(cas: 70-55-3Category: amides-buliding-blocks)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Category: amides-buliding-blocks

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The author of 《Direct Phenolysis Reactions of Unactivated Amides into Phenolic Esters Promoted by a Heterogeneous CeO2 Catalyst》 were Rashed, Nurnobi Md.; Siddiki, S. M. A. Hakim; Touchy, Abeda Sultana; Jamil, A. R. Md.; Poly, Sharmin Sultana; Toyao, Takashi; Maeno, Zen; Shimizu, Ken-ichi. And the article was published in Chemistry – A European Journal in 2019. Recommanded Product: 78191-00-1 The author mentioned the following in the article:

The direct catalytic esterification of amides that leads to the construction of C-O bonds through the cleavage of amide C-N bonds is a highly attractive strategy in organic synthesis. While aliphatic and aromatic alcs. can be readily used for the alcoholysis of activated and unactivated amides, the introduction of phenols is more challenging due to their lower nucleophilicity in the phenolysis of unactivated amides. Herein, phenols can be used for the phenolysis of unactivated amides into the corresponding phenolic esters using a simple heterogenous catalytic system based on CeO2 under additive-free reaction conditions was demonstrated. The method tolerates a broad variety of functional groups (>50 examples) in the substrates. Results of kinetic studies afforded mechanistic insights into the principles governing this reaction, suggesting that the cooperative effects of the acid-base functions of catalysts would be of paramount importance for the efficient progression of the C-N bond breaking process, and consequently, CeO2 showed the best catalytic performance among the catalysts explored. In the part of experimental materials, we found many familiar compounds, such as N-Methoxy-N-methylacetamide(cas: 78191-00-1Recommanded Product: 78191-00-1)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Recommanded Product: 78191-00-1

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Morgan, Timaeus E. F.; Riley, Leanne M.; Tavares, Adriana A. S.; Sutherland, Andrew published an article in 2021. The article was titled 《Automated radiosynthesis of cis- and trans-4-[18F]fluoro-L-proline using [18F]Fluoride》, and you may find the article in Journal of Organic Chemistry.COA of Formula: C11H24N2O The information in the text is summarized as follows:

The positron emission tomog. imaging agents cis- and trans-4-[18F]fluoro-L-proline are used for the detection of numerous diseases such as pulmonary fibrosis and various carcinomas. These imaging agents are typically prepared by nucleophilic fluorination of 4-hydroxy-L-proline derivatives, with [18F]fluoride, followed by deprotection. Although effective radiofluorination reactions have been developed, the overall radiosynthesis process is suboptimal due to deprotection methods that are performed manually, require multiple steps, or involve harsh conditions. Here we describe the development of two synthetic routes that allow access to precursors, which undergo highly selective radiofluorination reactions and rapid deprotection, under mild acidic conditions. These methods were found to be compatible with automation, avoiding manual handling of radioactive intermediates. After reading the article, we found that the author used tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8COA of Formula: C11H24N2O)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.COA of Formula: C11H24N2O

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Gopalsamy, Ariamala; Aulabaugh, Ann E.; Barakat, Amey; Beaumont, Kevin C.; Cabral, Shawn; Canterbury, Daniel P.; Casimiro-Garcia, Agustin; Chang, Jeanne S.; Chen, Ming Z.; Choi, Chulho; Dow, Robert L.; Fadeyi, Olugbeminiyi O.; Feng, Xidong; France, Scott P.; Howard, Roger M.; Janz, Jay M.; Jasti, Jayasankar; Jasuja, Reema; Jones, Lyn H.; King-Ahmad, Amanda; Knee, Kelly M.; Kohrt, Jeffrey T.; Limberakis, Chris; Liras, Spiros; Martinez, Carlos A.; McClure, Kim F.; Narayanan, Arjun; Narula, Jatin; Novak, Jonathan J.; O’Connell, Thomas N.; Parikh, Mihir D.; Piotrowski, David W.; Plotnikova, Olga; Robinson, Ralph P.; Sahasrabudhe, Parag V.; Sharma, Raman; Thuma, Benjamin A.; Vasa, Dipy; Wei, Liuqing; Wenzel, A. Zane; Withka, Jane M.; Xiao, Jun; Yayla, Hatice G. published an article in 2021. The article was titled 《PF-07059013: A Noncovalent Modulator of Hemoglobin for Treatment of Sickle Cell Disease》, and you may find the article in Journal of Medicinal Chemistry.Reference of N-Methoxy-N-methylacetamide The information in the text is summarized as follows:

Sickle cell disease (SCD) is a genetic disorder caused by a single point mutation (β6 Glu → Val) on the β-chain of adult Hb (HbA) that results in sickled Hb (HbS). In the deoxygenated state, polymerization of HbS leads to sickling of red blood cells (RBC). Several downstream consequences of polymerization and RBC sickling include vaso-occlusion, hemolytic anemia, and stroke. We report the design of a noncovalent modulator of HbS, clin. candidate PF-07059013 (23). The seminal hit mol. was discovered by virtual screening and confirmed through a series of biochem. and biophys. studies. After a significant optimization effort, we arrived at 23, a compound that specifically binds to Hb with nanomolar affinity and displays strong partitioning into RBCs. In a 2-wk multiple dose study using Townes SCD mice, 23 showed a 37.8% (±9.0%) reduction in sickling compared to vehicle treated mice. 23 (PF-07059013) has advanced to phase 1 clin. trials. The experimental part of the paper was very detailed, including the reaction process of N-Methoxy-N-methylacetamide(cas: 78191-00-1Reference of N-Methoxy-N-methylacetamide)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Reference of N-Methoxy-N-methylacetamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In 2022,Yan, Yu-Hang; Li, Wenfang; Chen, Wei; Li, Chao; Zhu, Kai-Rong; Deng, Ji; Dai, Qing-Qing; Yang, Ling-Ling; Wang, Zhenling; Li, Guo-Bo published an article in European Journal of Medicinal Chemistry. The title of the article was 《Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors》.Product Details of 683-57-8 The author mentioned the following in the article:

X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives, I [R1 = cyclopropyl, 4-pyridylmethyl, 2-(1-methyltetrazol-5-yl)sulfanylethyl, etc.; R2 = R3 = Me, cyclopropyl, Ph, etc.] was reported by considering how to engage with the active-site flexible loops and improve penetration into Gram-neg. bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallog. analyses. Of the tested ICA inhibitors, I [R1 = 4-pyridylmethyl, R2 = R3 = H] displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clin. isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphol. and internal structural changes of bacterial cells after treatment further demonstrated that I [R1 = 4-pyridylmethyl, R2 = R3 = H] crossed the outer membrane and reversed the activity of meropenem. Moreover, I [R1 = 4-pyridylmethyl, R2 = R3 = H] showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-neg. carbapenem resistance. The results came from multiple reactions, including the reaction of 2-Bromoacetamide(cas: 683-57-8Product Details of 683-57-8)

2-Bromoacetamide(cas: 683-57-8) can be used in preparation of (2-carbamoylmethoxy-5-chloro-benzyl)-carbamic acid tert-butyl ester. It was aslo used as precursor to dehydropeptidase I inactivator.Product Details of 683-57-8

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In 2022,Khiar-Fernandez, Nora; Zian, Debora; Vazquez-Villa, Henar; Martinez, R. Fernando; Escobar-Pena, Andrea; Foronda-Sainz, Roman; Ray, Manisha; Puigdomenech-Poch, Maria; Cincilla, Giovanni; Sanchez-Martinez, Melchor; Kihara, Yasuyuki; Chun, Jerold; Lopez-Vales, Ruben; Lopez-Rodriguez, Maria L.; Ortega-Gutierrez, Silvia published an article in Journal of Medicinal Chemistry. The title of the article was 《Novel Antagonist of the Type 2 Lysophosphatidic Acid Receptor (LPA2), UCM-14216, Ameliorates Spinal Cord Injury in Mice》.Product Details of 683-57-8 The author mentioned the following in the article:

Spinal cord injuries (SCIs) irreversibly disrupt spinal connectivity, leading to permanent neurol. disabilities. Current medical treatments for reducing the secondary damage that follows the initial injury are limited to surgical decompression and anti-inflammatory drugs, so there is a pressing need for new therapeutic strategies. Inhibition of the type 2 lysophosphatidic acid receptor (LPA2) has recently emerged as a new potential pharmacol. approach to decrease SCI-associated damage. Toward validating this receptor as a target in SCI, we have developed a new series of LPA2 antagonists, among which compound 54 (UCM-14216) stands out as a potent and selective LPA2 receptor antagonist (Emax = 90%, IC50 = 1.9 μM, KD = 1.3 nM; inactive at LPA1,3-6 receptors). This compound shows efficacy in an in vivo mouse model of SCI in an LPA2-dependent manner, confirming the potential of LPA2 inhibition for providing a new alternative for treating SCI.2-Bromoacetamide(cas: 683-57-8Product Details of 683-57-8) was used in this study.

2-Bromoacetamide(cas: 683-57-8) can be used in preparation of (2-carbamoylmethoxy-5-chloro-benzyl)-carbamic acid tert-butyl ester. It was aslo used as precursor to dehydropeptidase I inactivator.Product Details of 683-57-8

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of C4H9NO2In 2020 ,《Antibacterial Spiropyrimidinetriones with N-Linked Azole Substituents on a Benzisoxazole Scaffold Targeting DNA Gyrase》 was published in Journal of Medicinal Chemistry. The article was written by Basarab, Gregory S.; Doig, Peter; Eyermann, Charles J.; Galullo, Vincent; Kern, Gunther; Kimzey, Amy; Kutschke, Amy; Morningstar, Marshall; Schuck, Virna; Vishwanathan, Karthick; Zhou, Fei; Gowravaram, Madhusudhan; Hauck, Sheila. The article contains the following contents:

Herein, we report spiropyrimidinetriones (SPTs) incorporating N-linked azole substituents on a benzisoxazole scaffold with improved Gram-pos. antibacterial activity relative to previously described analogs. SPTs have an unusual spirocyclic architecture and represent a new antibacterial class of bacterial DNA gyrase and topoisomerase IV inhibitors. They are not cross-resistant to fluoroquinolones and other DNA gyrase/topoisomerase IV inhibitors used clin. The activity of the SPTs was assessed for DNA gyrase inhibition, and the antibacterial activity across Gram-pos. and Gram-neg. pathogens with N-linked 1,2,4-triazoles substituted on the 5-position provides the most worthwhile profile. Directed nucleophilic and electrophilic chem. was developed to vary this 5-position with carbon, nitrogen, or oxygen substituents and explore structure-activity relationships including those around a target binding model. Compounds with favorable pharmacokinetic parameters were identified, and two compounds demonstrated cidality in a mouse model of Staphylococcus aureus infection. After reading the article, we found that the author used N-Methoxy-N-methylacetamide(cas: 78191-00-1Synthetic Route of C4H9NO2)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Synthetic Route of C4H9NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《Efficient Copper(II)-Catalyzed Transamidation of Nonactivated Primary Carboxamides and Ureas with Amines》 was written by Zhang, Min; Imm, Sebastian; Baehn, Sebastian; Neubert, Lorenz; Neumann, Helfried; Beller, Matthias. Synthetic Route of C8H9NO2 And the article was included in Angewandte Chemie, International Edition in 2012. The article conveys some information:

A copper(II) catalyzed transamidation process using nonactivated primary carboxamides and ureas with amines is presented. For this technique, the Cu(OAc)2 is fairly inexpensive and convenient to use without special precautions. Fortunately, a wide range of amides, ureas, chiral amines can be synthesized from primary carboxamides and amines in good to excellent yields. By extension this protocol can be applied to the synthesis of amides, peptide, polyamides and heterocycles. In the part of experimental materials, we found many familiar compounds, such as 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Synthetic Route of C8H9NO2)

2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.“,” In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Synthetic Route of C8H9NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《Preparation of Weinreb amides using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM)》 was written by Hioki, Kazuhito; Kobayashi, Hiroko; Ohkihara, Rumi; Tani, Shohei; Kunishima, Munetaka. Synthetic Route of C13H26N2O4 And the article was included in Chemical & Pharmaceutical Bulletin on April 30 ,2004. The article conveys some information:

Weinreb amides were successfully prepared from the corresponding carboxylic acids by using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as a coupling reagent to form the activated ester, which then, reacted with N,O-dimethylhydroxylamine·HCl to form the amide. Methanol, iso-propanol and acetonitrile were useful solvents for the reaction because they solubilized DMT-MM. Weinreb amides of PhCO2H, 4-ClC6H4CO2H, PhCH:CHCO2H, PhCH(Me)CO2H, Cbz-Gly-OH, Boc-Leu-OH, Boc-Trp-OH, Boc-Pro-OH, PhCOCO2H and EtO2C(CH2)4CO2H were synthesized in moderate to very high yields.(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Synthetic Route of C13H26N2O4) was used in this study.

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Synthetic Route of C13H26N2O4 In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics