Tag: 100-200

Preparation of Primary Amides from Functionalized Organozinc Halides was written by Schade, Matthias A.;Manolikakes, Georg;Knochel, Paul. And the article was included in Organic Letters in 2010.COA of Formula: C7H5Cl2NO This article mentions the following:

Organozinc halides, which are prepared either by direct zinc insertion or halogen-magnesium exchange and subsequent transmetalation with ZnCl₂, react smoothly with com. available trichloroacetyl isocyanate to give, after hydrolysis, the corresponding primary amides. This method is compatible with a variety of functional groups such as an ester or a cyano group. Also heterocyclic-, alkenyl, and acetylenic zinc reagents are converted to the corresponding primary amides under these conditions. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4COA of Formula: C7H5Cl2NO).

3,4-Dichlorobenzamide (cas: 2670-38-4) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.COA of Formula: C7H5Cl2NO

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

Copper-Catalyzed Guanidinylation of Aryl Iodides: The Formation of N,N’-Disubstituted Guanidines was written by Cortes-Salva, Michelle;Nguyen, Be-Lan;Cuevas, Javier;Pennypacker, Keith R.;Antilla, Jon C.. And the article was included in Organic Letters in 2010.Safety of N,N-Diethylsalicylamide This article mentions the following:

A copper-catalyzed cross-coupling reaction of guanidine nitrate with aryl iodides was used for the formation of N,N’-disubstituted guanidines to be used as potential therapeutics for strokes. A relatively inexpensive com. available guanidine salt and a series of aryl iodides together with copper iodide and N,N-diethylsalicylamide as an efficient catalyst/ligand system provided a simple diarylation procedure. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Safety of N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Safety of N,N-Diethylsalicylamide

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

Cyclic guanidines as dual 5-HT_5A/5-HT₇ receptor ligands: Structure-activity relationship elucidation was written by Peters, Jens-Uwe;Luebbers, Thomas;Alanine, Alexander;Kolczewski, Sabine;Blasco, Francesca;Steward, Lucinda. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Synthetic Route of C7H7FN2O This article mentions the following:

The optimization of affinity and selectivity in a novel series of dual 5-HT_5A/5-HT₇ receptor ligands is described. Brain penetrant 2-aminodihydroquinazolines, such as I, with low nanomolar affinities were identified. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5Synthetic Route of C7H7FN2O).

2-Amino-4-fluorobenzamide (cas: 119023-25-5) 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. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Synthetic Route of C7H7FN2O

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

Design and Synthesis of LM146, a Potent Inhibitor of PB1 with an Improved Selectivity Profile over SMARCA2 was written by Melin, Lea;Gesner, Emily;Attwell, Sarah;Kharenko, Olesya A.;van der Horst, Edward H.;Hansen, Henrik C.;Gagnon, Alexandre. And the article was included in ACS Omega in 2021.Name: 6-Chloro-2-aminobenzamide This article mentions the following:

PB1 is a bromodomain-containing protein hypothesized to act as the nucleosome-recognition subunit of the PBAF complex. Although PB1 is a key component of the PBAF chromatin remodeling complex, its exact role has not been elucidated due to the lack of potent and selective inhibitors. Chem. probes that target specific bromodomains within the complex would constitute highly valuable tools to characterize the function and therapeutic pertinence of PB1 and of each of its bromodomains. Here, we report the design and synthesis of lead compound LM146, which displays strong stabilization of the second and fifth bromodomains of PB1 as shown by DSF. LM146 does not interact with bromodomains outside of sub-family VIII and binds to PB1(2), PB1(5), and SMARCA2B with K_D values of 110, 61, and 2100 nM, resp., providing a ~34-fold selectivity profile for PB1(5) over SMARCA2. In the experiment, the researchers used many compounds, for example, 6-Chloro-2-aminobenzamide (cas: 54166-95-9Name: 6-Chloro-2-aminobenzamide).

6-Chloro-2-aminobenzamide (cas: 54166-95-9) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Name: 6-Chloro-2-aminobenzamide

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

A convenient synthesis of 5-substituted tetrahydro-1,4,3-oxathiazine 4,4-dioxides was written by Grunder-Klotz, Evelyne;Humbert, Paul;Ehrhardt, Jean Daniel. And the article was included in Heterocycles in 1993.SDS of cas: 5339-69-5 This article mentions the following:

Tetrahydrooxathiazine dioxides I (R¹ = H, Me, Ph; R² = H, Me; R³ = 4-ClC₆H₄, 4-MeOC₆H₄, CH₂Ph, Bu, iso-Pr) were prepared in a 1-pot synthesis by the reaction of N-alkyl- or N-arylsulfonamide dianions with gaseous HCHO. Thus, MeSO₂Cl condensed with 4-ClC₆H₄NH₂ to give MeSO₂NHC₆H₄Cl-4 which was reacted with 2.1 equivalent BuLi and then HCHO(g) to give I (R¹, R² = H, R³ = 4-ClC₆H₄). The stability and some reactions of these heterocyclic compounds were also described. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5SDS of cas: 5339-69-5).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.SDS of cas: 5339-69-5

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

A mild and convenient oxidation of aryl nitriles to aryl amides by aqueous sodium perborate was written by Reed, Kathryn L.;Gupton, John T.;Solarz, Traci L.. And the article was included in Synthetic Communications in 1990.Name: 3,4-Dichlorobenzamide This article mentions the following:

Treatment of aryl nitriles with NaBO₃.4H₂O in aqueous dioxane gives the corresponding benzamides in 13-85% yields. E.g., 3,5-Cl₂C₆H₃CN gives 74% 3,5-Cl₂C₆H₃CONH₂. The effect of substrate structure on yield is discussed. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Name: 3,4-Dichlorobenzamide).

3,4-Dichlorobenzamide (cas: 2670-38-4) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Name: 3,4-Dichlorobenzamide

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

Indiplon: Treatment of insomnia GABA-A agonist was written by Sorbera, L. A.;Castaner, J.;Martin, L.. And the article was included in Drugs of the Future in 2003.HPLC of Formula: 325715-13-7 This article mentions the following:

Six different synthetic routes are investigated for the preparation of N-Methyl-N-[3-[3-[2-thienylcarbonyl]pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]a cetamide (Indiplon) and its potential use as a drug for treatment of insomnia is evaluated. Indiplon is a GABA-A receptor partial agonist that promotes sleep by enhancing the inhibitory activity of GABA through specific binding to the BZ1 or α₁ subunit of the GABA-A receptor. Indiplon has been shown to be safe and well tolerated and is currently being developed in two formulations to treat all insomnia complaints, including sleep initiation, night awakenings and total sleep maintenance. In the experiment, the researchers used many compounds, for example, N-(3-Acetylphenyl)-N-methylacetamide (cas: 325715-13-7HPLC of Formula: 325715-13-7).

N-(3-Acetylphenyl)-N-methylacetamide (cas: 325715-13-7) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.HPLC of Formula: 325715-13-7

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

Directed ortho metalation of N,N-diethyl benzamides. Methodology and regiospecific synthesis of useful contiguously tri- and tetra-substituted oxygenated aromatics, phthalides and phthalic anhydrides was written by De Silva, S. O.;Reed, J. N.;Billedeau, R. J.;Wang, X.;Norris, D. J.;Snieckus, V.. And the article was included in Tetrahedron in 1992.Recommanded Product: N,N-Diethylsalicylamide This article mentions the following:

Full exptl. details for the directed ortho metalation approach to o-RC₆H₄CONEt₂ (R = e.g., CO₂H, CO₂Me, CONEt₂, CHO, OH, Br, F, organometallic) and contiguously 1,2,3- and 1,2,3,4-substituted benzamides, I and II (R = CHO, CO₂H, OH), and III and IV [R = Me, (RR) = CH₂; R¹ = e.g., Me, CO₂H] are given. The efficient conversion of benzamides I–IV (R or R¹ = H) into phthalides (e.g., V; Z = H₂) and phthalic anhydrides (e.g., V; Z = O), compounds previously available by demanding, classical methods, is detailed. A short synthesis of isoochracinic acid is described. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Recommanded Product: N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Recommanded Product: N,N-Diethylsalicylamide

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

Polyazanaphthalenes. III. Some derivatives of 1,3,5-and 1,3,8-triazanaphthalene was written by Oakes, V.;Pascoe, R.;Rydon, H. N.. And the article was included in Journal of the Chemical Society in 1956.Recommanded Product: 50608-99-6 This article mentions the following:

Derivatives of 1,3,5- and 1,3,8-triazanaphthalenes were prepared from the corresponding 2,4-dihydroxy compounds 3-Aminopicolinic acid (I), m. 210°, (26 g.) was prepared by adding aqueous NaOBr, from 56 g. Br and 350 ml. 15% NaOH, to a solution of 50 g. quinolinimide in 1 l. of ice-cold 10% NaOH, and was kept at room temperature for 1 hr. and at 85° for 1 hr., cooled, adjusted to pH 5 with 50% H₂SO₄, filtered, added to Cu(OAc)₂ and freed with H₂S. Some 2-aminonicotinic acid (II) was obtained on filtration. The Et ester of I, m. 132°, and hydrazine hydrate gave 3-aminopicolinic hydrazide (III), m. 103°. III and acetone gave acetone 3-aminopicolinoylhydrazone, m. 172°, while NalO₃ and in aqueous NH₃ gave 3-aminopicolinamide, m. 184°; picrate, m. 214°. Similarly, the Et ester of II, m. 96°, 2-aminonicotinic hydrazide, m. 176° and acetone 2-aminonicotinoylhydrazone (IV), m. 179° were prepared IV and NaIO₃ in aqueous NH₃ gave 2-aminonicotinaldehyde. 2-R-4-R’ disubstituted 1,3,5-triazanaphthalene (IVa) (R = R’ = OH) (V) 6 g., m. above 380°, was prepared by heating a mixture of 13 g. I and 7 g. (H₂N)₂CO at 190-200° for 30 min., dissolving the product in 200 ml. 2N NaOH and precipitating with CO₂. Distillation of V with Zn dust gave 1,3,4-triazaindene, m. 152°. 2,4-Dihydroxy-1,3,8-triazanaphthalene (VI), m. 361°, was prepared by the method of Robins and Hitchings (C.A. 50, 2604c). IVa (R = R’ == Cl) (VII) 3.25 g., m. 173°, was prepared by heating a mixture of 5 g. V, 75 ml. POCl₃ and 10 ml. Et₃N (VIII) for 6 hrs. VII was also obtained when PhNMe₂ was used in place of VIII. Et₂NH gave IVa (R = Cl, R’ = EtPhN), m. 168°. Reduction of VII over PtO₂ or in the presence of MgO gave impure 1,3,5-triazanaphthalene, (picrate m. 191°). Other IVa were prepared by the reaction of VII with (H₂N)₂CS, EtSNa, and RONa were (R, R’-m.p. given): HS, HS (IX), 340°; EtS, EtS, 56°; MeO, MeO, 138°; EtO, EtO, 110°. A mixture of 3 g. Me₂SO₄, 250 mg. V, and 10 ml. 2N NaOH was shaken, allowed to stand overnight, NH₄OH was added, the solution extracted with CHCl₃ and on evaporation gave 140 mg. 1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-1,3,5-triazanaphthalene, m. 246°. NH₃ and 1 g. VII in 20 g. of boiling PhOH gave after cooling and treatment with 25% NaOH, IVa (R = R’ = NH₂), m. 318°. Similarly in dioxane NH₃ and VII gave IVa (R = Cl, R’ = NH₂) (X), m. 265°. X and (H₂N)₂CS gave IVa (R = SH, R’ = NH₂) (XI), m. 344°. IX and NH₄OH gave XI. IVa (R = H, R’ = NH₂) (XII), m. 224° was prepared by heating XI with Raney Ni in alc. NH₃. IVa (R = H, R’ = HO) (XIII), m.p. 342° was prepared by heating 50 mg. XII with 8 ml. 5N HCl at 100° for 30 min. followed by treatment with 2N Na₂CO₃, and by heating I and HCONH₂ at 130° for 2.5 hrs. and at 180° for 2.5 hrs. IVa (R = Cl, R’ = Et₂N), m. 82°, and IVa [R = Cl, R’ = Et₂N(CH₂)₃NH], m. 128° were prepared by heating the corresponding amine with VII in dioxane. N₂H₄.H₂O and VII in cold dioxane gave on filtration 2 (or 4)-hydrazino-4(or 2)-hydroxy-1,3,5-triazanaphthalene, m. 385° and dilution of the dioxane filtrate with ethanol gave IVa (R = R’ = H₂NNH), m. 266°. Similarly, the following derivatives of 2-R-4-R’ substituted 1,3,8-triazanaphthalene were prepared (R, R’, m.p. given). HO, HO, 361°; Cl, Cl, (XIV) 160°; EtS, EtS, 76°; NH₂, NH₂, 342°; Cl, NH₂, above 360°; HS, HO, 360°; H, HO, 255-6°. Reduction of XIV over PtO₂ or in the presence of MgO gave 5,6,7,8-tetrahydro-2,4-dimethoxy-1,3,8-triazanaphthalene. 3-Aminoisonicotinic acid formed a hydrazide, m. 187°. In the experiment, the researchers used many compounds, for example, 3-Aminopicolinamide (cas: 50608-99-6Recommanded Product: 50608-99-6).

3-Aminopicolinamide (cas: 50608-99-6) 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. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Recommanded Product: 50608-99-6

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

Gold-Catalyzed Intermolecular [4+2] Annulation of 2-Ethynylanilines with Ynamides: An Access to Substituted 2-Aminoquinolines was written by Zhao, Ximei;Song, Xinlong;Jin, Hongming;Zeng, Zhongyi;Wang, Qian;Rudolph, Matthias;Rominger, Frank;Hashmi, A. Stephen K.. And the article was included in Advanced Synthesis & Catalysis in 2018.Computed Properties of C9H13NO2S This article mentions the following:

A gold-catalyzed intermol. [4+2] annulation of easily accessible 2-ethynylanilines with ynamides offered a highly regioselective, modular, efficient and atom-economical strategy for the synthesis of substituted 2-aminoquinolines such as I [R¹ = H, 6-F, 6-Cl, 6-CF₃, 6-Me; R² = Ph, 4-MeOC₆H₄, 2-thienyl, etc.; R³ = Me, n-Pr, Bn, etc.; R⁴ = Tosyl, Mesyl, Benzenesulfonyl] in up to 93% yield. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Computed Properties of C9H13NO2S).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Computed Properties of C9H13NO2S

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