55379-75-4

Usage

Also known as

β-phenylalanine nitrile

Structure

Consists of a nitrile group, an amino group, and a phenyl group attached to a propanenitrile chain

Role

Important intermediate in the synthesis of pharmaceuticals and agrochemicals

Usage

Commonly used as a building block in the production of various compounds

Precursor

Used in the synthesis of β-phenethylamine

Bioactive compound

Found in many plants and animals with physiological and pharmacological effects

Versatile

Valuable compound with various applications in different industries, especially in organic chemistry.

Upstream product

• 143-33-9 sodium cyanide 
• 122-78-1 phenylacetaldehyde 
• 151-50-8 potassium cyanide 
• 65732-65-2 2-(2-Nitro-phenylsulfanylamino)-3-phenyl-propionamide 
• 66913-75-5 2-cyano-3-phenylaziridine 
• 159517-27-8 (R)-2-amino-3-phenylpropanenitrile 
• 93554-83-7 α-aminophenylpropiononitrile hydrochloride 
• 140-29-4 phenylacetonitrile 
• 74-90-8 hydrogen cyanide 
• 1188327-50-5 diethylaluminium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 64-04-0 phenethylamine 
• 773837-37-9 sodium cyanide 

Downstream Products

• 123437-81-0 3-Benzyl-5-(4-methoxy-phenyl)-6-methyl-1-oxy-pyrazin-2-ylamine 
• 132087-50-4 3-Benzyl-7-methoxy-9H-indeno[1,2-b]pyrazin-2-ylamine 
• 63-91-2 L-phenylalanine 
• 673-06-3 D-(R)-phenylalanine 
• 5241-58-7 D-Phenylalaninamide 
• 75543-73-6 (S)-2-amino-3-phenyl-1-propylamine 
• 181376-74-9 (+)-(R)-N-(1-cyano-2-phenyl-ethyl)-acetamide 
• 934168-99-7 2-(3-allyl-1-thioureido)-3-phenylpropipnitrile 
• 4360-47-8 cinnamonitrile 
• 114496-03-6 12-benzyl-8-hydroxy-2-(4-hydroxybenzyl)-11H-benz[f]imidazo[1,2-a]quinoxalin-3-one 
• 132063-70-8 3-Benzyl-5-(4-isopropoxy-phenyl)-1-oxy-6-(2-trityloxy-ethyl)-pyrazin-2-ylamine 
• 132063-71-9 2-Benzyl-8,10-bis-benzyloxy-4-oxy-5,6-dihydro-benzo[f]quinoxalin-3-ylamine 
• 132063-68-4 2-Benzyl-8-benzyloxy-4-oxy-5,6-dihydro-benzo[f]quinoxalin-3-ylamine 
• 132063-69-5 2-Benzyl-9-methoxy-4-oxy-6,7-dihydro-5H-benzo[3,4]cyclohepta[1,2-b]pyrazin-3-ylamine 

Relevant academic research and scientific papers

IMPROVED METHODS, KITS, COMPOSITIONS AND DOSING REGIMENS FOR THE USE OF HETEROCYCLIC INHIBITORS OF ERK1 AND ERK2

The present application provides improved compositions, methods, kits and dosing regimens for the use of heterocyclic compounds and pharmaceutically acceptable salts, prodrugs, solvates, hydrates, or stereoisomers thereof. These compositions, methods, kit

METHODS OF TREATING LIVER FIBROSIS USING CALPAIN INHIBITORS

Disclosed herein are methods of treating liver fibrosis by administering calpain inhibitors to subjects in need thereof.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Small molecule calpain modulator compounds, including their pharmaceutically acceptable salts, can be included in pharmaceutical compositions. The compounds can be useful in inhibiting calpain, or competitive binding with calpastatin, by contacting them with CAPN1, CAPN2, and/or CAPN9 enzymes residing inside a subject. The compounds and composition can also be administered to a subject in order to treat a fibrotic disease or a secondary disease state or condition of a fibrotic disease.

Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions

Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.

HETEROCYCLIC INHIBITORS OF ERK1 AND ERK2 AND THEIR USE IN THE TREATMENT OF CANCER

The present application provides novel heterocyclic compounds and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful for inhibiting ERK1/2. By administering to a patient in need a

A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins

Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).

Continuous-flow oxidative cyanation of primary and secondary amines using singlet oxygen

Primary and secondary amines can be rapidly and quantitatively oxidized to the corresponding imines by singlet oxygen. This reactive form of oxygen was produced using a variable-temperature continuous-flow LED-photoreactor with a catalytic amount of tetraphenylporphyrin as the sensitizer. α- Aminonitriles were obtained in good to excellent yields when trimethylsilyl cyanide served as an insitu imine trap. At 25°C, primary amines were found to undergo oxidative coupling prior to cyanide addition and yielded secondary α-aminonitriles. Primary α-aminonitriles were synthesized from the corresponding primary amines for the first time, by an oxidative Strecker reaction at -50 °C. This atom-economic and protecting-group-free pathway provides a route to racemic amino acids, which was exemplified by the synthesis of tert-leucine hydrochloride from neopentylamine. The mild synthesis of imines paves the way to aminonitriles and amino acids. Aerobic oxidation of primary and secondary amines in a continuous photoreactor with singlet oxygen generated insitu led to the rapid formation of imines, which were quantitatively trapped as α-aminonitriles (see scheme; TMS=trimethylsilyl). Benzylic and primary α-aminonitriles, precursors for amino acids, could be efficiently produced in three minutes.

Method of making imidazole-2-thiones

The present invention provides a method of making an imidazole-2-thione which comprises the steps of reacting a vicinal diamine with a compound having a thiocarbonyl moiety and oxidizing the resulting reaction product to obtain said imidazole-2-thione.

PROCESS FOR THE RACEMISATION OF ENANTIOMERICALLY ENRICHED ALPHA-AMINO NITRILES

Process for the racemisation of an enantiomerically enriched α-amino nitrile characterized in that the enantiomerically enriched α-amino nitrile is contacted with a lewis acid catalyst. Preferably an aprotic solvent is used. The lewis acid catalyst preferably comprises a metal chosen from main group elements IA-IVA of the Periodic Table (CAS version), the transition metals and the lanthanides, in particular Al, Ti, Zr, or lanthanides. The catalsyt for example has the general structure MnXpSqLr, and preferably is chosen from the group of aluminum alkoxides, aluminum alkyls, lanthanide alkoxydes and lanthanocenes. The racemisation may be performed in combination with a resolution process, for instance in combination with an enzymatic or a crystallization induced resolution process, preferably in situ, for instance in situ in a crystallization induced asymmetric transformation process.

Process for the preparation of enantiomerically enriched compounds

1. Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0,5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa. The enantiomerically enriched nitrile starting material may a.o. be prepared by enzymatic resolution, classical resolution, resolution via preferential crystallization, diastereomeric synthesis, catalytic asymmetric synthesis or dehydratation of amino acid amides.