6319-70-6

Upstream product

• 124-40-3 dimethyl amine 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 4870-65-9 2-bromophenylacetic acid 
• 108-86-1 bromobenzene 
• 33229-89-9 N,N-dimethylglycine ethyl ester 
• 101-97-3 Ethyl 2-phenylethanoate 
• 541-41-3 chloroformic acid ethyl ester 
• 611-74-5 N,N-dimethylbenzamide 
• 59624-58-7 Lithium; (E)-1-ethoxy-2-phenyl-ethenolate 
• 85506-17-8 (2R,4S,5R)-2-O-(N,N-dimethylhydroxylamino)-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one 
• 50-00-0 formaldehyd 
• 6097-58-1 ethyl 2-phenyl-2-aminoacetate 

Downstream Products

• 1353887-53-2 (S)-2-(dimethylamino)-2-phenylacetic acid hydrochloride 
• 58685-78-2 2-(dimethylamino)-2-phenylacetic acid (hydrochloride salt) 
• 94409-78-6 (2-hydroxy-1-phenyl-ethyl)-trimethyl-ammonium; iodide 
• 20245-69-6 (+/-)-dimethyl-(β-hydroxy-α-phenylethyl)amine 

Relevant academic research and scientific papers

Further reactions of phenyldimethylsilyllithium with N,N-dimethylamides

Phenyldimethylsilyllithium reacts with several N,N-dimethylamides, and the intermediates, formulated here as successively a carbene and an α-silyllithium species, may be trapped with nucleophiles and electrophiles, respectively, although not always with t

Discovery of inhibitors of the mitotic kinase TTK based on N-(3-(3-sulfamoylphenyl)-1H-indazol-5-yl)-acetamides and carboxamides

TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at positions 3 and 5, respectively, establishing a novel chemical class culminating in identification of 72 (CFI-400936). This potent inhibitor of TTK (IC50 = 3.6 nM) demonstrated good activity in cell based assay and selectivity against a panel of human kinases. A co-complex TTK X-ray crystal structure and results of a xenograft study with TTK inhibitors from this class are described.

KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME

The present teachings provide a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. Also described are a pharmaceutical composition and method of use thereof.

The extraordinary reactions of phenyldimethylsilyllithium with N,N-disubstituted amides

The reactions of the silyllithium reagent with tertiary amides was discussed. The enediamines were easily isomerized from cis to trans, easily oxidized to dienediamines and were hydrolyzed to α-aminoketones. If the two equivalents of the silyllithium reagent were used, the product was an α-silylamine. The results show that each member of the homologous series of amides gives rise to a substantially different product.

Use of Carboxylic Acids as Chiral Solvating Agents for the Determination of Optical Purity of Chiral Amines by NMR Spectroscopy

Optically pure mandelic acid, Mosher's acid, and N-(3,5-dinitrobenzoyl)phenylglycine have been used as chiral solvating agents to induce nonequivalence in the 1H NMR spectra of several diamines, amino acid esters, amino alcohols, and other amines.The identity of the chiral solvating agent and the stoichiometry of the solvation complexes that yield the greatest nonequivalence varies with the nature of the substrate.

Kinetic Resolution of Racemic β-Hydroxy Amines by Enantioselective N-Oxide Formation

A practical and fairly general procedure for the kinetic resolution of β-hydroxy tertiary amines is described.It involves the selective oxidation of one enantiomer to the N-oxide by using tert-butyl hydroperoxide (TBHP) and a chiral catalyst prepared by mixing 2 parts of titanium isopropoxide (Ti(O-i-Pr)4 and 1.2 parts of either (+)- or (-)-diisopropyl tartrate (DIPT).The product N-oxide and the unreacted amino alcohol are then easily separated by trituration or organic/aqueous solvent extractions, and chromatography is avoided.The oxidations are generally run to 60percent conversion and the results for 21 different amino alcohols are given.The enantiomeric excess of the slow reacting (i.e., recovered) enantiomer of the amino alcohol often exceeds 90percent.Among the more interesting substrates are the natural product ubine (95percent ee) (18), N-methylephedrine (95percent ee) (15), N-methylpseudoephedrine (93percent ee) (16), cis-2-(dimethylamino)cyclohexanol (>95percent ee) (13), trans-2-(dimethylamino)cyclohexanol (92percent ee) (12), N-benzylbevantolol (85percent ee) (27), and N-benzylpropranolol (32percent ee) (21).The latter two examples are β-blocker precursors.One of the most important characteristics of this new route to enantiomerically pure β-hydroxy amines is its predictability.Thus, in all cases examined to date, when using (+)-DIPT the absolute configuration at the carbinol center in the slow reacting enantiomer is always the same .A study of how the titanium/tartrate ratio, water, catalyst/substrate ratio, and temperature effect this reaction is discussed.

A CHIRAL REAGENT IDUCING ASYMMETRY IN ELECTROPHILIC AMINATION REACTIONS

The chiral amination reagent (-)-1 was prepared from (-)-ephedrine, configurationally determined by X-ray structure analysis and reacted with carbon nucleophiles to yield the optically active amines 4a-d with up to 44percent ee.