5470-15-5

Usage

InChI:InChI=1/C22H27NO5/c1-12(2)28-22(25)19-13(3)23-15-7-6-8-16(24)21(15)20(19)14-9-10-17(26-4)18(11-14)27-5/h9-12,20,23H,6-8H2,1-5H3

Upstream product

• 64-18-6 formic acid 
• 95-76-1 m,p-dichloroaniline 
• 2258-42-6 formyl acetic anhydride 
• 149-73-5 trimethyl orthoformate 
• 99-54-7 3,4-dichloronitrobenzene 
• 33876-96-9 N-(3,4-dichlorophenyl)-1-imidazolecarboxamide 
• 77287-34-4 formamide 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 123-91-1 1,4-dioxane 
• 71144-20-2 (3,4-Dichloranilino)phenyl-acetonitril 

Downstream Products

• 69753-52-2 N-(3,4-dichloro-phenyl)-N-formyl-N'-methyl-urea 
• 40750-59-2 3,4-dichloro-N-methylaniline 
• 333986-28-0 N-(3-chloropropyl)-N-(3,4-dichlorophenyl)formamide 
• 333986-31-5 N-(3-chloropropyl)-N-(3,4-dichlorophenyl)-1-(methylsulfonyl)piperidine-4-carboxamide 
• 333986-49-5 N-(3-chloropropyl)-N-(3,4-dichlorophenyl)-1-(methylsulfonyl)piperidine-4-carboxamide 
• 333993-36-5 N-{3-[4-(4-aminobenzyl)-1-piperidinyl]propyl}-N-(3,4-dichlorophenyl)-1-(methylsulfonyl)-4-piperidinecarboxamide 
• 333993-35-4 N-(3,4-dichlorophenyl)-1-(methylsulfonyl)-N-{3-[4-(4-nitrobenzyl)-1-piperidinyl]propyl}-4-piperidinecarboxamide 

Relevant academic research and scientific papers

Mild Access to N-Formylation of Primary Amines using Ethers as C1 Synthons under Metal-Free Conditions

A new synthetic protocol has been developed for the synthesis of N-formamide derivatives using ethers as a C1 synthon under metal-free reaction conditions. The reaction is proposed to proceed through C?H functionalization, C?O cleavage, and C?N bond formation. This protocol is applicable to a variety of primary amines resulting in N-formamides in moderate to good yields. 1,4-dioxane was chosen as best C1 synthon after screening with various ethers. Mechanistic studies disclosed that the reaction proceeds through a radical pathway. While using α-amino ketones a α-alkylation product was formed rather than formylation. By replacing dioxane with Tetramethylethylenediamine (TMEDA) under standard conditions also gave the N-formamide derivatives in moderate yields. (Figure presented.).

Mesoporous silica SBA-15 functionalized with acidic deep eutectic solvent: A highly active heterogeneous N-formylation catalyst under solvent-free conditions

Mesoporous silica SBA-15 functionalized with N-methylpyrrolidonium-zinc chloride based deep eutectic solvent (DES) is found to be a more efficient and reusable catalyst for a convenient N-formylation of a variety of amines at room temperature. N-Formylation of primary, secondary as well as heterocyclic amines have been carried out in good to excellent yields by treatment with formic acid in low loading of DES/SBA-15 an environmentally benign catalyst for the first time. The DES/SBA-15 catalyst, which possesses both Br?nsted and Lewis acidities as well as an active SBA-15 support, makes this procedure quite simple, reusable, more convenient and practical. This catalyst was tolerant of a wide range of functional groups, and it can be reused for four runs without obvious deactivation.

Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions

The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. In the current report we disclosed a consecutive Lossen rearrangement/transamidation reaction in which unactivated hydroxamic acids were converted into N-substituted formamides in a one-pot manner under catalyst- and additive-free conditions. One feature of this novel transformation is that the formamide plays triple roles in the reaction by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products. Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives. The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions. Not only monosubstituted formamides were synthesized from hydroxamic acids, but also N,N-disubstituted formamides were obtained when secondary amines were used as precursors.

Novel method for synthesizing N-substitute amide derivative

The invention discloses a novel method for synthesizing an N-substitute amide derivative. The novel method is characterized by comprising the steps that at the air atmosphere, no catalyst or alkali or other any additives are added, an organic amine compound shown in a formula (I) is adopted as a reaction substrate, a solvent shown in a formula (II) is adopted as an acylation reagent, an acylation reaction is performed under the reaction temperature of 120-150 DEG C to generate the N-substitute amide derivative shown in a formula (III), and the equation is shown in the description. The novel method has the advantages that environmental protection is achieved, and post-treatment and product separation are easy; the range of the substrate is wide, and the substrate can be primary amine and can also be secondary amine; the solvent can be amide and can also be carboxylic acid, and the solvent can be adopted as the acylation reagent to participate in the reaction; the reaction efficiency is high, and the majority of reactions can reach the quantified yield; water and air have no effect on the reaction, inert gas shielding is not needed, and operation is easy.

Method for synthesizing formamide compound

The invention discloses a method for synthesizing a formamide compound. The synthetic method comprises the following steps: taking carbamyl imidazole compound as a raw material, preparing the formamide compound in a mixed solution of tetrahydrofuran and water by taking hydroboron as a reducing agent. The catalyst hydroboron used in the method disclosed by the invention has the advantages of environment friendliness, stable performance, high conversion rate and the like. Moreover, the initial raw material and used reagents are simple and readily available, the cost is low, and the operation is simple and feasible. Therefore, the route is a route which is low in cost, simple in operation and suitable for industrial production.

An efficient reduction of N-substituted carbonylimidazolides into formamides by NaBH4

A novel, simple and versatile protocol was investigated for highly efficient synthesis of formamides through reducing N-substituted carbonylimidazolides by NaBH4 under mild reaction conditions. By this method, not only carboxylic acids or isocyanates, but also amines can readily access formamides with high yields.

Highly efficient rhodium-catalyzed transfer hydrogenation of nitroarenes into amines and formanilides

An efficient and selective rhodium-catalyzed transfer hydrogenation of nitroarenes with formic acid as the hydrogen source to give amines or formanilides has been developed. The addition of iodide ion accelerates the reaction, which can take place at room temperature. Georg Thieme Verlag Stuttgart New York.

Deep eutectic solvent promoted highly efficient synthesis of N, N'-diarylamidines and formamides

A deep eutectic solvent was used as a dual catalyst and reaction medium for the efficient N-formylation of aromatic amines without hazardous organic solvent and catalyst. Treatment of aromatic amines with trimethyl orthoformate and formic acid in deep eutectic solvent at 70 °C gives the corresponding N-formyl derivatives in good to excellent yields. This simple ammonium deep eutectic solvent, easily synthesized from choline chloride and SnCl2, with 100% atom economy and making it applicable to industry and laboratory. Furthermore, heating the trimethyl orthoformate and aromatic primary amines in the deep eutectic solvent results in formation of the corresponding N,N'-diarylamidines in high yields.

CHEMICAL COMPOUNDS

This invention relates to non-steroidal compounds that are modulators of androgen receptor, and also to the methods for the making and use of such compounds.

CCR5 antagonists as anti-HIV-1 agents. Part 3: Synthesis and biological evaluation of piperidine-4-carboxamide derivatives

Replacement of the 5-oxopyrrolidin-3-yl fragment in the previously reported lead structure with a 1-acetylpiperidin-4-yl group led to the discovery of a novel series of potent CCR5 antagonists. Introduction of small hydrophobic substituents on the central phenyl ring increased the binding affinity, providing low to sub-nanomolar CCR5 antagonists. The selected compound 11f showed excellent antiviral activity against CCR5-using HIV-1 replication in human peripheral blood mononuclear cells (EC50 = 0.59 nM) and an acceptable pharmacokinetic profile in dogs.