46050-30-0

Upstream product

• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 621-82-9 Cinnamic acid 
• 7664-41-7 ammonia 
• 4192-77-2 ethyl cinnamate 
• 1401072-41-0 2-(9H-fluoren-9-ylidene)-5-oxo-3-phenylpyrazolidin-2-ium-1-ide 
• 145091-94-7 5-phenyl-4,5-dihydro-pyrazol-3-one 
• 100-52-7 benzaldehyde 
• 22838-46-6 methyl 3-amino-3-phenylpropionate hydrochloride 
• 14440-98-3 N-(benzyloxycarbonyl)-DL-3-amino-3-phenylpropionic acid 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 17193-27-0 N^β-Benzyloxycarbonyl-DL-β-phenyl-β-alanin-amid 

Downstream Products

• 621-79-4 cinnamamide 
• 208655-12-3 (S)-1-phenyl-1,3-propanediamine 
• 669087-29-0 (3S)-3-amino-3-phenylpropanamide 
• 126590-55-4 tert-butyl N-(3-amino-3-oxo-1-phenyl-propyl)carbamate 
• 4888-74-8 1-phenyl-1,3-propanediamine 
• 110425-61-1 3-acetamido-3-phenylpropanamide 

Relevant academic research and scientific papers

Intermolecular aminocarbonylation of alkenes using concerted cycloadditions of iminoisocyanates

The aminocarbonylation of alkenes is a powerful method for accessing the β-amino carbonyl motif that remains underdeveloped. Herein, the development of intermolecular aminocarbonylation reactivity of iminoisocyanates with alkenes is presented. This includes the discovery of a fluorenone-derived reagent, which was effective for many alkene classes and facilitated derivatization. Electron-rich substrates were most reactive, and this indicated that the LUMO of the iminoisocyanate is reacting with the HOMO of the alkene. Computational and experimental results support a concerted asynchronous [3 + 2] cycloaddition involving an iminoisocyanate, which was observed for the first time by FTIR under the reaction conditions. The products of this reaction are complex azomethine imines, which are precursors to valuable β-amino carbonyl compounds such as β-amino amides and esters, pyrazolones, and bicyclic pyrazolidinones. A kinetic resolution of the azomethine imines by enantioselective reduction (s = 13.43) allows access to enantioenriched products. Overall, this work provides a new tool to convert alkenes into β-amino carbonyl compounds.

Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors

Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo[2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-π interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N1, N1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFRL858R reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists.

Highly enantioselective enzymatic resolution of aromatic β-amino acid amides with Pd-catalyzed racemization

The kinetic resolution of an aromatic β-amino acid amide 3a-d via N-acylation was explored with two lipases, Candida antarctica lipase A (CALA) and Pseudomonas stutzeri lipase (PSL). The PSL-catalyzed resolution proceeded with excellent enantioselectivity