Category: amides-buliding-blocks

The author of 《Hydrogenative Cyclopropanation and Hydrogenative Metathesis》 were Peil, Sebastian; Guthertz, Alexandre; Biberger, Tobias; Fuerstner, Alois. And the article was published in Angewandte Chemie, International Edition in 2019. Formula: C4H9NO2 The author mentioned the following in the article:

The unusual geminal hydrogenation of a propargyl alc. derivative with [CpXRuCl] as the catalyst entails formation of piano stool ruthenium carbenes in the first place; these reactive intermediates can be intercepted with tethered alkenes to give either cyclopropanes or cyclic olefins as the result of a formal metathesis event. The course of the reaction is critically dependent on the substitution pattern of the alkene trap. The results came from multiple reactions, including the reaction of N-Methoxy-N-methylacetamide(cas: 78191-00-1Formula: C4H9NO2)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Formula: C4H9NO2

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

The author of 《A Green and Sustainable Approach for Selective Halogenation of Anilides, Benzanilides, Sulphonamides and Heterocycles》 were Lakshmireddy, V. M.; Naga Veera, Y.; Reddy, T. J.; Rao, V. J.; China Raju, B.. And the article was published in Asian Journal of Organic Chemistry in 2019. COA of Formula: C9H7ClF3NO The author mentioned the following in the article:

An efficient green and sustainable protocol was devised for the selective oxidative halogenation of acetanilides, benzanilides, sulfonamides and heterocyclic compounds to afford haloanilides and halosulfonamides I [R = COMe, COPh, SO2Ph; R1 = Cl, Br; R2 = H, F; R3 = H, i-Pr, CF3, etc.; R4 = H, F, Br, etc.], haloimidazoles, haloindoles, halothiazoles and 1,2,4-triazole e.g. II and halopyridines III [R5 = NH2, NHCOMe, Br, etc.; R6 = NH2, Cl, Br, etc.; R7 = H, NH2, NH(Me)2, NHCOMe; R8 = H, Cl, Br] using easily available NaX as a halogen source and oxone as a powerful oxidant. The present protocol was simple and environmentally benign to conduct the laboratory scale halogenations and could be extended to prepare industrially important compounds In the experiment, the researchers used many compounds, for example, N-(2-Chloro-4-(trifluoromethyl)phenyl)acetamide(cas: 247170-19-0COA of Formula: C9H7ClF3NO)

N-(2-Chloro-4-(trifluoromethyl)phenyl)acetamide(cas: 247170-19-0) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.COA of Formula: C9H7ClF3NO

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

Kondo, Mitsuru; Okubo, Takashi; Asami, Akiko; Noro, Shin-Ichiro; Yoshitomi, Tomomichi; Kitagawa, Susumu; Ishii, Tomohiko; Matsuzaka, Hiroyuki; Seki, Kenji published an article on January 15 ,1999. The article was titled 《Rational synthesis of stable channel-like cavities with methane gas adsorption properties: [{Cu2(pzdc)2(L)}n] (pzdc = pyrazine-2,3-dicarboxylate; L =a pillar ligand)》, and you may find the article in Angewandte Chemie, International Edition.Application of 64479-78-3 The information in the text is summarized as follows:

Porous coordination networks were designed in prepared copper complexes [{Cu2(pzdc)2(L)}n] (pzdc = pyrazine-2,3-dicarboxylate; L = pillar ligand pyrazine, 4,4′-bipyridyl, N-4-pyridinyl-4-pyridinecarboxamide). The structure of [{Cu2(pzdc)2(pyz)}.2H2O]n (1) was determined by x-ray crystallog. The complex consists of a pillared layer structure with a two-dimensional sheet of [Cu(pzdc)2]n and pillar pyrazine ligands that bridge each sheet. The channels are occupied by water mols. Thermal dehydration of 1 at 100-260° resulted in a stable phase which retained the porous network without decomposition (powder XRD study). Methane adsorption capabilities of the coordination networks were studied. Increased methane absorption activity for pillar ligands 4,4′-bipyridyl and N-4-pyridinyl-4-pyridinecarboxamide is consistent with the larger channel sizes of these complexes. The activity is comparable to that of zeolites and other reported stable porous coordination networks. The experimental process involved the reaction of N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Application of 64479-78-3)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.Application of 64479-78-3

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

In 2017,Australian Journal of Chemistry included an article by Roxburgh, Matthew A. D.; Zaiter, Samantha; Hudson, Xina I. B.; Mullaney, Benjamin R.; Clements, John E.; Moubaraki, Boujemaa; Murray, Keith S.; Neville, Suzanne M.; Kepert, Cameron J.. Synthetic Route of C11H9N3O. The article was titled 《Structure and Magnetic Studies on a Series of Two-Dimensional Iron(II) Framework Materials with Varying Ligand Characteristics》. The information in the text is summarized as follows:

Targeting the general (4,4)-grid structural motif, the authors prepared seven new coordination polymers in the general family [Fe(NCX)2(L)2]·(guest) (L = bis-pyridyl-type bridging ligands; X = S, Se) as an extension of the well-established spin crossover framework (SCOF) family. In all cases, the (4,4)-grid topol. is formed by the bridging of octahedral Fe(II) sites in the equatorial plane by bis-pyridyl ligands of varying length, flexibility, and intermol. interaction capacity. In particular, the six ligands n-(4-pyridyl)isonicotinamide (pin), trans-1,2-bis(4-pyridyl)ethene (tvp), 1,2-dibromo-1,2-bis(4-pyridyl)ethane (dbbpe), bis(4-pyridyl)-1,2,4,5-tetrazine (bptz), 4,4′-bis(pyridyl)acetylene (bpac), and 1,4-bis(4-pyridylethynyl)benzene (bpeben) were used. The seven complexes, [Fe(NCS)2(pin)2]·2(MeCN) (pin-S), [Fe(tvp)2(NCS)2]·1/2(tvp)·(CH2CH2OH) (tvp-S), [Fe(dbbpe)2(NCS)2]·6(CH3CN) (dbbpe-S), [Fe(NCS)2(bptz)2]·2(CHCl3)·6(H2O) (bptz-S), [Fe(NCSe)2(bptz)2]·4(CHCl3)·(EtOH)·(H2O) (bptz-Se), [Fe(NCS)2(bpac)2]·2(PrOH) (bpac-S), and [Fe(NCS)2(bpeben)2]·2(CHCl3) (bpeben-S) all form (4,4)-grids of varying size that are arranged in a parallel stacked topol. Despite being in the [FeN6] coordination environment known to be conducive to spin crossover, these materials all remain high-spin with thermal variation. These results are discussed in context with the large family of SCOFs that show varied spin crossover behaviors. The results came from multiple reactions, including the reaction of N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Synthetic Route of C11H9N3O)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.Synthetic Route of C11H9N3O

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

Almaliti, Jehad; Miller, Bailey; Pietraszkiewicz, Halina; Glukhov, Evgenia; Naman, C. Benjamin; Kline, Toni; Hanson, Jeffrey; Li, Xiaofan; Zhou, Sihong; Valeriote, Frederick A.; Gerwick, William H. published an article in European Journal of Medicinal Chemistry. The title of the article was 《Exploration of the carmaphycins as payloads in antibody drug conjugate anticancer agents》.Quality Control of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The author mentioned the following in the article:

Antibody-drug conjugates (ADCs) represent a new dimension of anticancer chemotherapeutics, with warheads to date generally involving either antitubulin or DNA-directed agents to achieve low-to sub-nanomolar potency. However, other potent cytotoxins working by different pharmacol. mechanisms are under investigation, such as α,β-epoxyketone based proteasome inhibitors. These proteasome active agents are an emerging class of anticancer drug that possesses ultra-potent cytotoxicity to some cancer cell lines. The carmaphycins are representatives of this latter class that we isolated and characterized from a marine cyanobacterium, and these as well as several synthetic analogs exhibit this level of potency. In the current work, we investigated the use of these highly potent cytotoxic compounds as warheads in the design of novel ADCs. We designed and synthesized a library of carmaphycin B analogs that contain amine handles, enabling their attachment to an antibody linker. The basicity of these incorporated amine handles was shown to strongly affect their cytotoxic properties. Linear amines resulted in the greatest reduction in cytotoxicity whereas less basic aromatic amines retained potent activity as demonstrated by a 4-sulfonylaniline derivative These investigations resulted in identifying the P2 residue in the carmaphycins as the most suitable site for linker attachment point, and hence, we synthesized a highly potent analog of carmaphycin B that contained a 4-sulfonylaniline handle as an attachment point for the linker antibody. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Quality Control of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.Quality Control of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

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

Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideOn May 10, 2012 ,《Small Molecule Suppression of Carbapenem Resistance in NDM-1 Producing Klebsiella pneumoniae》 appeared in ACS Medicinal Chemistry Letters. The author of the article were Worthington, Roberta J.; Bunders, Cynthia A.; Reed, Catherine S.; Melander, Christian. The article conveys some information:

The already considerable global public health threat of multidrug-resistant Gram-neg. bacteria has become even more of a concern following the emergence of New Delhi metallo-β-lactamase (NDM-1) producing strains of Klebsiella pneumoniae and other Gram-neg. bacteria. As an alternative approach to the traditional development of new bactericidal entities, we have identified a 2-aminoimidazole-derived small mol. that acts as an antibiotic adjuvant and is able to suppress resistance of a NDM-1 producing strain of K. pneumoniae to imipenem and meropenem, in addition to suppressing resistance of other β-lactam nonsusceptible K. pneumoniae strains. The small mol. is able to lower carbapenem min. inhibitory concentrations by up to 16-fold, while exhibiting little bactericidal activity itself. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.

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

Product Details of 70298-88-3On October 12, 2011 ,《Light-Induced Spin Change by Photodissociable External Ligands: A New Principle for Magnetic Switching of Molecules》 was published in Journal of the American Chemical Society. The article was written by Thies, Steffen; Sell, Hanno; Schuett, Christian; Bornholdt, Claudia; Naether, Christian; Tuczek, Felix; Herges, Rainer. The article contains the following contents:

Magnetic bistability in spin-crossover materials generally is a collective phenomenon that arises from the cooperative interaction of a large number of microscopic magnetic moments within the crystal lattice in the solid state. The authors now report on individual mols. in homogeneous solution that are switched between the diamagnetic and paramagnetic states at room temperature by light-driven coordination-induced spin-state switching (LD-CISSS). Switching of the coordination number (and concurrently of the spin state) was achieved by using Ni-porphyrin as a square-planar platform and azopyridines as photodissociable axial ligands. The square-planar Ni-porphyrin is diamagnetic (low-spin, S = 0), and all complexes with axial ligands are paramagnetic (high-spin, S = 1). Association constants were determined for all conceivable 1:1 and 1:2 porphyrin/azopyridine complexes. The binding constants of the trans azopyridines are larger than those of the corresponding cis isomers. Thus, upon irradiation with UV light (365 nm, trans → cis) and visible light (455 nm, cis → trans), switching of the magnetic properties was achieved. Upon substitution of the azopyridines at the 4- and 4′-positions with larger substituents, the difference in trans and cis association constants, and thus the switching efficiency, was increased. A photoinduced, reversible switching between 20 and 68% paramagnetic Ni species in solution was achieved with iso-Pr substituents at room temperature In addition to this study using 2,2-Dimehtyl-N-pyridin-3-yl-propionamide, there are many other studies that have used 2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3Product Details of 70298-88-3) was used in this study.

2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Product Details of 70298-88-3

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

《Introduction of the amide function into 1,3,2-dioxaphospholenes with pentavalent phosphorus》 was published in Journal of the American Chemical Society in 1970. These research results belong to Ramirez, Fausto; Bauer, J.; Telefus, C. David. Application In Synthesis of 2-Hydroxy-N-phenylacetamide The article mentions the following:

Carbamoyl-1,3,2-dioxaphospholenes with pentavalent P were synthesized from α-oxo aldehydes, isocyanates, and trialkyl phosphites. The phospholenes were converted into phosphate esters of β-oxo-α-hydroxyamides. These underwent rapid hydrolyses to β-oxo-α-hydroxyamides. The experimental process involved the reaction of 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Application In Synthesis of 2-Hydroxy-N-phenylacetamide)

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. Application In Synthesis of 2-Hydroxy-N-phenylacetamide

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