54879-88-8

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzyl-2,2-dimethoxyethanamine is used as a synthetic intermediate for the preparation of guanidylimidazole and guanidylimidazoline derivatives. These derivatives have potential applications as antimalarial agents, targeting the Plasmodium parasite responsible for malaria. N-BENZYL-2,2-DIMETHOXYETHANAMINE's reactivity and structural features make it a valuable building block in the development of new drugs to combat this global health issue.

InChI:InChI=1/C11H17NO2/c1-13-11(14-2)9-12-8-10-6-4-3-5-7-10/h3-7,11-12H,8-9H2,1-2H3

Upstream product

• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 100-46-9 benzylamine 
• 97-97-2 chloroacetaldehyde dimethyl acetal 
• 54879-74-2 (2,2-Dimethoxy-ethyl)-[1-phenyl-meth-(Z)-ylidene]-amine 
• 51673-84-8 dimethoxyacetaldehyde 
• 22483-09-6 2,2-dimethoxyethylamine 
• 100-52-7 benzaldehyde 
• 216578-83-5 (RS)-N-benzyl-2-chloro-2-fluoroethanamide 
• 958643-13-5 N-benzyl-N-(2-chloro-2-fluoroethyl)amine 
• 64792-80-9 2-(benzoylamino)acetaldehyde dimethyl acetal 

Downstream Products

• 95821-37-7 benzyl-[2,2-bis-(3,4-dimethoxy-phenyl)-ethyl]-amine 
• 119369-68-5 9,10-bis-benzylaminomethyl-2,3,6,7-tetramethoxy-9,10-dihydro-anthracene 
• 119926-19-1 N-benzyl-N'-(1-phenyl-propyl)-ethylenediamine 
• 23269-10-5 1-benzyl-1H-imidazole-2-thione 
• 141213-93-6 2-amino-6--5-nitro-4(3H)-pyrimidinone 
• 307002-13-7 benzyl (benzyl)(2,2-dimethoxyethyl)carbamate 
• 753478-33-0 2-amino-1-benzyl-3-cyanopyrrole 
• 945257-27-2 C₁₉H₂₃NO₃ 
• 945257-39-6 C₂₃H₃₁O₅N 
• 14052-84-7 7-benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 166947-03-1 benzyl benzyl(2-oxoethyl)carbamate 
• 307002-62-6 benzyl (benzyl){2-[2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl]-2-(1H-indol-3-yl)ethyl}carbamate 
• 307002-18-2 ethyl hydrogen 2-{2-[(benzyl)(benzyloxycarbonyl)amino]-1-(1H-indol-3-yl)ethyl}malonate 

Relevant academic research and scientific papers

Six-Step Gram-Scale Synthesis of the Human Immunodeficiency Virus Integrase Inhibitor Dolutegravir Sodium

A short and practical synthesis for preparing the active pharmaceutical ingredient dolutegravir sodium was developed. The convergent strategy starts from (R)-3-amino-1-butanol and establishes the BC ring system in a 76% isolated yield over four steps. Ring A was constructed by a one-pot 1,4-addition to diethyl-(2E/Z)-2-(ethoxymethylidene)-3-oxobutandioate and subsequent MgBr2·OEt2-mediated regioselective cyclization. Amide formation with 2,4-difluorobenzylamine was either performed from the free carboxylic acid or through aminolysis of the corresponding ethyl ester. Final salt formation afforded dolutegravir sodium in a 48-51% isolated yield (HPLC purity of 99.7-99.9%) over six linear steps.

Design, Synthesis, and Biological Evaluation of Imidazopyrazinone Derivatives as Antagonists of Inhibitor of Apoptosis Proteins (IAPs)

Apoptosis inhibitor (IAP) proteins are overexpressed in many cancers and implicated in tumor growth, so the development of antagonist that disrupts with the binding of IAP to their partner protein is a promising therapeutic strategy. In an effort to incre

Synthesis of tetrahydroisoquinolines through TiCl4-mediated cyclization and Et3SiH reduction

A versatile and efficient telescoped reaction sequence for the synthesis of tetrahydroisoquinolines (THIQs) is reported that uses TiCl4 to promote cyclization of a benzylaminoacetal derivative and Et3SiH for reduction of the intermediate 4-hydroxy-THIQ. This method is complimentary to the classical Pomeranz-Fritsch and related reactions since it tolerates electron-withdrawing substituents and allows access to 8-substituted THIQs.

Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz-Fritsch Cyclization

Isoquinolines (IQs) and their derivatives are present in many natural products and biologically active small molecules. Herein, we report a modified procedure for the classical Pomeranz-Fritsch protocol, which expands the scope of 1,2-dihydroisoquinoline (DHIQ) products. 1,2-DHIQs are an attractive branch point for the synthesis of IQs, but because of their innate reactivity, they have remained difficult to prepare. We demonstrate that the Fujioka/Kita conditions, combining trimethylsiyltriflate (TMSOTf) and an amine base, activate dimethylacetals required for Pomeranz-Fritsch cyclization under sufficiently mild conditions to prepare a broad range of 1,2-DHIQ products. We also demonstrate the synthetic value of these DHIQs by further functionalization to either reduced tetrahydroisoquinoline (THIQ) or fully aromatized IQ natural products.

Preparation method of polysubstituted pyrrole compound

The invention discloses a preparation method of a polysubstituted pyrrole compound of 1-benzyl-2-amino-3-cyan pyrrole derivative. Malononitrile, benzaldehyde and aminoacetaldehyde dimethanol are usedas starting raw materials to prepare a target product through reductive amination, loop closing and amino derivatization. The compound has potential bioactivity.

Ultrasound assisted one-pot synthesis of benzo-fused indole-4,9-dinones from 1,4-naphthoquinone and α-aminoacetals

A one-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinone with α-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[f]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated.

Electrochemical deoxygenation of aromatic amides and sulfoxides

The electrochemical deoxygenation of a broad range of aromatic amides was achieved under mild conditions on lead cathodes. Under the optimized reaction conditions, acetal, thienyl, and ether moieties are tolerated. Furthermore, the reduction protocol can be applied to aromatic and aliphatic sulfoxides to obtain the corresponding sulfides. For both aromatic amides and sulfoxides, the deoxygenation reaction ensues without the use of expensive catalysts or hazardous reducing agents. Owing to the high selectivity of the process, simple extraction is sufficient to isolate the product from the substrate. The straightforward purification protocol, the coformation of water, and the use of electric current instead of reducing agents render our method environmentally friendly and economically beneficial. Copyright

PROCESS FOR THE PREPARATION OF PRAZIQUANTEL

The present disclosure describes a novel, cost-effective process for preparation of a 4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino-[2,1-a]isoquinoline derivatives. Specifically, it discloses a process for the preparation of the anthelmintic drug praziquantel through the use of a novel intermediate, 2-[(2,2-dimethoxyethyl)benzyl amino]-N-phenethylacetamide. This present disclosure also describes a novel crystalline form of 4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline.

Flexible access to conformationally-locked bicyclic morpholines

A preparatively accessible route to a series of conformationally-locked bicyclic morpholines has been developed. This flexible approach allows for diversification in order for a small array of lead-like scaffolds to be synthesised from readily available k

Antimalarial activities of new guanidylimidazole and guanidylimidazoline derivatives

A series of new guanidylimidazole derivatives was prepared and evaluated in mice and Rhesus monkeys infected with malarial sporozoites. The majority of the new compounds showed poor metabolic stability and weak in vitro activities in three clones of Plasm