7291-02-3

Usage

Uses

Used in Pharmaceutical Industry:
BenzaMide, N,N-diMethyl-3-nitrois used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows it to be a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
BenzaMide, N,N-diMethyl-3-nitrois also utilized in the synthesis of dyes, where its aromatic and nitro groups contribute to the color and properties of the resulting dyes. It can be used to produce a variety of dyes with different shades and characteristics.
Used in Organic Chemistry:
BenzaMide, N,N-diMethyl-3-nitroserves as an important intermediate in the production of various organic compounds. Its reactivity and functional groups make it a valuable precursor in organic synthesis, enabling the creation of a wide range of chemical products.

InChI:InChI=1/C9H10N2O3/c1-10(2)9(12)7-4-3-5-8(6-7)11(13)14/h3-6H,1-2H3

Upstream product

• 110-86-1 pyridine 
• 3984-14-3 N,N-dimethylsulfamide 
• 121-92-6 3-nitrobenzoic acid 
• 124-40-3 dimethyl amine 
• 121-90-4 m-nitrobenzoic acid chloride 
• 74-88-4 methyl iodide 
• 71-43-2 benzene 
• 137-26-8 Thiram 
• 7409-18-9 3-nitrobenzylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 506-59-2 N,N-dimethylammonium chloride 
• 18503-89-4 N,N-dimethylformamide diisopropyl acetal 
• 121-73-3 3-Nitrochlorobenzene 
• 585-79-5 m-nitrobromobenzene 

Downstream Products

• 123-56-8 Succinimide 
• 87329-71-3 N-methyl-N-succinimidomethyl-m-nitrobenzamide 
• 63833-39-6 2,4-dimethyl-5-(3-nitro-benzoyl)-pyrrole-3-carboxylic acid ethyl ester 
• 33322-60-0 3-amino-N,N-dimethylbenzamide 
• 99-61-6 3-nitro-benzaldehyde 
• 25900-61-2 3-amino-N-methylbenzamide 
• 83247-19-2 2-Dimethylamino-2-ethoxy-2-(3-nitrophenyl)acetonitril 
• 13749-73-0 3-Nitrothiobenzoesaeure-O-ethylester 

Relevant academic research and scientific papers

Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals

We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.

Heterocyclic IDH mutant inhibitor, preparation method and application thereof

The invention discloses a heterocyclic IDH mutant inhibitor, a preparation method and application thereof, belongs to the field of medicines, and particularly relates to a s-triazine compound with structural characteristics of a general formula (I) or a pharmaceutically acceptable salt thereof, a pharmaceutical composition, a preparation method of the s-triazine compound, and application of the s-triazine compound or the pharmaceutically acceptable salt and the pharmaceutical composition as isocitrate dehydrogenase 2 (IDH2) mutant inhibitors. The compound disclosed by the invention has an obvious inhibiting effect on the activity of an IDH2 mutant (mIDH2), can effectively inhibit the process of catalyzing alpha-ketoglutaric acid to generate 2-hydroxyglutaric acid by the mIDH2, and can be used for preventing and/or treating various related diseases including cancers caused by IDH2 mutation.

2-Arylamino-6-ethynylpurines are cysteine-targeting irreversible inhibitors of Nek2 kinase

Renewed interest in covalent inhibitors of enzymes implicated in disease states has afforded several agents targeted at protein kinases of relevance to cancers. We now report the design, synthesis and biological evaluation of 6-ethynylpurines that act as covalent inhibitors of Nek2 by capturing a cysteine residue (Cys22) close to the catalytic domain of this protein kinase. Examination of the crystal structure of the non-covalent inhibitor 3-((6-cyclohexylmethoxy-7H-purin-2-yl)amino)benzamide in complex with Nek2 indicated that replacing the alkoxy with an ethynyl group places the terminus of the alkyne close to Cys22 and in a position compatible with the stereoelectronic requirements of a Michael addition. A series of 6-ethynylpurines was prepared and a structure activity relationship (SAR) established for inhibition of Nek2. 6-Ethynyl-N-phenyl-7H-purin-2-amine [IC50 0.15 μM (Nek2)] and 4-((6-ethynyl-7H-purin-2-yl)amino)benzenesulfonamide (IC50 0.14 μM) were selected for determination of the mode of inhibition of Nek2, which was shown to be time-dependent, not reversed by addition of ATP and negated by site directed mutagenesis of Cys22 to alanine. Replacement of the ethynyl group by ethyl or cyano abrogated activity. Variation of substituents on the N-phenyl moiety for 6-ethynylpurines gave further SAR data for Nek2 inhibition. The data showed little correlation of activity with the nature of the substituent, indicating that after sufficient initial competitive binding to Nek2 subsequent covalent modification of Cys22 occurs in all cases. A typical activity profile was that for 2-(3-((6-ethynyl-9H-purin-2-yl)amino)phenyl)acetamide [IC50 0.06 μM (Nek2); GI50 (SKBR3) 2.2 μM] which exhibited >5-10-fold selectivity for Nek2 over other kinases; it also showed > 50% growth inhibition at 10 μM concentration against selected breast and leukaemia cell lines. X-ray crystallographic analysis confirmed that binding of the compound to the Nek2 ATP-binding site resulted in covalent modification of Cys22. Further studies confirmed that 2-(3-((6-ethynyl-9H-purin-2-yl)amino)phenyl)acetamide has the attributes of a drug-like compound with good aqueous solubility, no inhibition of hERG at 25 μM and a good stability profile in human liver microsomes. It is concluded that 6-ethynylpurines are promising agents for cancer treatment by virtue of their selective inhibition of Nek2. This journal is

WEE1 KINASE INHIBITORS AND METHODS OF TREATING CANCER USING THE SAME

A compound, or a pharmaceutically acceptable salts or prodrugs thereof, having the chemical structure (I) and methods of using these compounds to inhibit WEE1 kinase and treat cancer in a subject.

POCl3 promoted metal-free synthesis of tertiary amides by coupling of carboxylic acids and N,N-disubstituted formamides

Herein we report a robust and synthetically useful catalyst-free amination methodology by the coupling of carboxylic acids and N-substituted formamides using POCl3 as a promoter. Versatile amides with a wide array of substituent groups were prepared within only 1 h in good to excellent yields. And even multi-substituted aromatic carboxylic acids could give the desired products with satisfactory results.

Development of Potent Pyrazolopyrimidinone-Based WEE1 Inhibitors with Limited Single-Agent Cytotoxicity for Cancer Therapy

WEE1 kinase regulates the G2/M cell-cycle checkpoint, a critical mechanism for DNA repair in cancer cells that can confer resistance to DNA-damaging agents. We previously reported a series of pyrazolopyrimidinones based on AZD1775, a known WEE1 inhibitor, as an initial investigation into the structural requirements for WEE1 inhibition. Our lead inhibitor demonstrated WEE1 inhibition in the same nanomolar range as AZD1775, and potentiated the effects of cisplatin in medulloblastoma cells, but had reduced single-agent cytotoxicity. These results prompted the development of a more comprehensive series of WEE1 inhibitors. Herein we report a series of pyrazolopyrimidinones and identify a more potent WEE1 inhibitor than AZD1775 and additional compounds that demonstrate that WEE1 inhibition can be achieved with reduced single-agent cytotoxicity. These studies support that WEE1 inhibition can be uncoupled from the potent cytotoxic effects observed with AZD1775, and this may have important ramifications in the clinical setting where WEE1 inhibitors are used as chemosensitizers for DNA-targeted chemotherapy.

Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols and N-substituted Formamides Using a Co–Al Based Heterogeneous Catalyst

Present work reports the direct synthesis of amides from oxidative coupling of benzyl alcohols with various N-substituted formamides using a cobalt-hydrotalcite (Co-HT) derived catalyst. The Co-HT derived catalysts (Co-HT-2, Co-HT-3 and Co-HT-4 having Co2+/Al3+ molar ratio in the catalyst preparation mixture as 1/1, 2/1 and 3/1 respectively) were prepare following a co-precipitation method and characterized well by powder XRD, XPS, FEG-SEM, EDS, DTG–TGA, FT-IR and N2 physisorption measurements. A range of functional amides were obtained in good yields from oxidative coupling of various substituted benzyl alcohols and a range of N-substituted formamides using Co-HT-3 catalyst and oxidant TBHP. Mechanistic investigation suggests that the amidation reaction is associated with the formation and coupling of radical species. Furthermore, the Co-HT derived catalyst was easily recoverable and recyclable with retained high catalytic activity towards the oxidative coupling of benzyl alcohol with DMF. Graphical Abstract: [Figure not available: see fulltext.].

Oxidative amidation of benzaldehydes and benzylamines with: N -substituted formamides over a Co/Al hydrotalcite-derived catalyst

The present work describes a highly efficient synthetic strategy for amides via oxidative coupling of benzaldehydes or benzylamines with N-substituted formamides using a heterogeneous Co/Al hydrotalcite-derived catalyst in the presence of TBHP. A series of Co/Al hydrotalcite-derived catalysts (Cat-2, Cat-3, and Cat-4 with the Co2+/Al3+ molar ratio in the synthesis mixture as 1/1, 2/1 and 3/1) have been prepared by a simple co-precipitation method and characterized using powder XRD, XPS, FEG-SEM, EDS, FT-IR, DTG-TGA and N2 physical adsorption techniques. Among the as-prepared catalysts, Cat-3 exhibited excellent catalytic activity towards the direct amidation of benzaldehydes as well as benzylamines bearing various substituents into the corresponding amides at 100 °C using TBHP as an oxidant. The mechanistic investigation of the amidation reaction revealed that the reaction follows a radical pathway. Furthermore, the catalyst is easily separable and recyclable without considerable loss in catalytic activity.

Synthesis method of amide aryl compound

The invention relates to a synthesis method of an amide aryl compounds. According to the method, Ru-(p-cymene) C12 is taken as a catalyst, K2S2O8 is taken as an oxidizing agent, Xantphos is taken as a ligand, one reactant (N, N-dialkyl formamide) is taken

Pd(PPh3)4 catalyzed amide compound synthesis method

The invention relates to a Pd(PPh3)4 catalyzed amide compound synthesis method. The synthesis method takes carboxylic acid as the substrate, and adopts N-substituted formamide as the amine source to synthesize an amide compound under the catalysis of Pd(PPh3)4. The method is widely applicable to substrates with different functional groups. The amide compound efficiently constructed by the invention is an important skeleton of many organic molecules, drugs, peptides, bioactive molecules and natural products. The synthesis method provided by the invention provides a widely applicable preparation method for synthesis of the compounds.