1131-83-5

Upstream product

• 55-21-0 benzamide 
• 107-13-1 acrylonitrile 
• 352-96-5 3-aminopropionitrile fumarate salt 
• 98-88-4 benzoyl chloride 
• 2079-89-2 β-aminopropionitrile monofumarate salt 
• 151-18-8 2-cyanoethylamine 
• 3232-12-0 N,N-bis(2-cyanoethyl)benzamide 

Downstream Products

• 114352-61-3 N-[2-(1H-tetrazol-5-yl)-ethyl]-benzamide 
• 30761-30-9 β-benzamidothiopropionamide 
• 3965-98-8 3-(benzoylamino)propionamidine hydrochloride 
• 95-02-3 5-(aminomethyl)-2-methylpyrimidin-4-amine 

Relevant academic research and scientific papers

Synthesis of novel amide and urea derivatives of thiazol-2-ethylamines and their activity against Trypanosoma brucei rhodesiense

2-(2-Benzamido)ethyl-4-phenylthiazole (1) was one of 1035 molecules (grouped into 115 distinct scaffolds) found to be inhibitory to Trypanosoma brucei, the pathogen causing human African trypanosomiasis, at concentrations below 3.6 μM and non-toxic to mammalian (Huh7) cells in a phenotypic high-throughput screen of a 700,000 compound library performed by the Genomics Institute of the Novartis Research Foundation (GNF). Compound 1 and 72 analogues were synthesized in this lab by one of two general pathways. These plus 10 commercially available analogues were tested against T. brucei rhodesiense STIB900 and L6 rat myoblast cells (for cytotoxicity) in vitro. Forty-four derivatives were more potent than 1, including eight with IC50 values below 100 nM. The most potent and most selective for the parasite was the urea analogue 2-(2-piperidin-1-ylamido)ethyl-4-(3-fluorophenyl)thiazole (70, IC50 = 9 nM, SI > 18,000). None of 33 compounds tested were able to cure mice infected with the parasite; however, seven compounds caused temporary reductions of parasitemia (≥97%) but with subsequent relapses. The lack of in vivo efficacy was at least partially due to their poor metabolic stability, as demonstrated by the short half-lives of 15 analogues against mouse and human liver microsomes.

KOtBu-Catalyzed Michael Addition Reactions Under Mild and Solvent-Free Conditions

Designed transition metal complexes predominantly catalyze Michael addition reactions. Inorganic and organic base-catalyzed Michael addition reactions have been reported. However, known base-catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side-reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu-catalyzed Michael addition reactions. This simple inorganic base efficiently catalyzes the Michael addition of underexplored acrylonitriles, esters and amides with (oxa-, aza-, and thia-) heteroatom nucleophiles. This catalytic process proceeds under solvent-free conditions and at room temperature. Notably, this protocol offers an easy operational procedure, broad substrate scope with excellent selectivity, reaction scalability and excellent TON (>9900). Preliminary mechanistic studies revealed that the reaction follows an ionic mechanism. Formal synthesis of promazine is demonstrated using this catalytic protocol.

Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds

Conjugate additions of non-nucleophilic N-containing compounds such as amides, thioamides, sulfonamides, and electron-poor anilines with different Michael acceptors can be promoted through the use of tributylphosphine. The range of useful pKa's of nucleophiles has been established (pKa25) and new insights into the mechanism proposed.

Reaction of Chromium (Fischer) Carbenes and Sulfilimines

The photochemical reactions of alkoxychromium (Fischer) carbenes and sulfilimines lead to imidates in fair to excellent yields.Aromatic, heteroaromatic, and alkylsulfilimines, the latter bearing functional groups such as cyano, sulfone, ether, ester, and dioxolane groups, gave the corresponding imidates in good to excellent yield.However, acyl- and sulfonyl-substituted sulfilimines did not react with chromium carbenes, except for sulfilimines bearing ethoxycarbonyl and phthalimidylamino groups.A variety of differently substituted chromium carbene complexes bearing alkyl, cycloalkyl, styryl, allyl, and alkynyl groups attached either at the carbene carbon or at the oxygen also gave imidates in good yields.For α,β-unsaturated carbenes, the exclusive 1,2-addition of the sulfilimines nitrogen was observed at room temperature, in contrast to the behavior of other nitrogen nucleophiles which are reported to add in 1,4-fashion under these reaction conditions.In turn, optically active imidates of the type ArN=C(OR*)Me can be prepared efficiently by utilizing the corresponding chiral alkoxy group on the carbene moiety.The reactions above also occur in the dark but reaction times are considerably longer.N-Halosulfilimines reacted with alkoxychromium carbenes to yield N-acylsulfilimines instead of the expected N-haloimidates.Based upon a set of thermal and photochemical reactions between N-haloimidates and diphenyl sulfide in the absence of chromium complexes, the complex (CO)5CrNCMe is proposed to be responsible for this novel reaction of N-haloimidates and diphenyl sulfide.

Dithio and thiono esters, LVII: Synthesis of dithio and thiono esters of N-protected β- and γ-amino acids

The N-protected β-aminonitriles 1 were transformed into the imidoester or thiolimidoester hydrochlorides 2 or 3 according to Pinner and sulfhydrolyzed with H2S to give the N-protected β-amino thiono esters 4 or dithio esters 5. Alkylation of th

Acylation of Dibasic Compounds Containing Amino Amidine and Aminoguanidine Functions

The site of acylation in difunctional compounds containing an amine and either an amidine or guanidine can be determined from the ultraviolet absorption spectrum of the acylated product.If the amidine or guanidine has been acylated, the product possesses a chromophore that is pH dependent, whereas if an amide was formed, the chromophore is independent of pH.