7462-76-2

Usage

InChI:InChI=1/C8H8ClNO/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11)

Upstream product

• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 4410-31-5 (RS)-mandelamide 
• 6476-18-2 4-phenyl-pyrrolidine-2,3,5-trione 
• 7732-18-5 water 
• 14380-61-1 hypochlorite 
• 1336-21-6 ammonium hydroxide 
• 2912-62-1 α-chlorophenylacetyl chloride 
• 532-28-5 (RS)-mandelonitrile 
• 401582-20-5 2-chloro-N-(4-methoxybenzyl)-2-phenylethanamide 

Downstream Products

• 7253-67-0 (R,S)-1-(1-piperidino)phenylacetamide 
• 1733-63-7 1,2,2-triphenylethan-1-one 
• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 856065-63-9 optically inactive 2.3-diphenyl-succinic acid diamide 
• 100542-70-9 (4-chloro-phenylsulfanyl)-phenyl-acetic acid amide 
• 15146-07-3 meso-1,2-dicyano-1,2-diphenylethane 
• 15307-93-4 N-phenyl-2,6-dichloroaniline 
• 312757-92-9 [3-cyano-4-(2-methoxyphenyl)-6-phenylpyridin-2-ylsulfanyl]phenylacetamide 

Relevant academic research and scientific papers

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

METHOD OF FORMING CARBONYL COMPOUND AND DEPROTECTION METHOD OF AMIDE-BASED COMPOUND USING A CLEAVAGE REACTION OF CARBON-NITROGEN BOND

The present invention relates to a preparation method of a carbonyl compound and a method for removing nitrogen-end protective group of an amide-based compound. The carbonyl compound is prepared by having a photocatalytic reaction of an amine-based group using water and an oxidizing agent. Therefore, the preparation method can prepare a carbonyl compound by usefully cutting carbon-nitrogen bonds at mild conditions, and such cutting reaction of carbon-nitrogen bonds can be usefully used for removing a protective group combined to an amide-based compound including amide or sulfonyl amide having carbon-nitrogen bonds.COPYRIGHT KIPO 2016

Formation of Carbonyl Compounds from Amines through Oxidative C-N Bond Cleavage using Visible Light Photocatalysis and Applications to N-PMB-Amide Deprotection

A method has been developed for C-N bond cleavage that utilizes visible light photocatalysis. The process, which utilizes 1 mol% of the ruthenium complex Ru(bpy)3Cl2 as the photocatalyst, potassium persulfate (K2S2O8) as the oxidant and water/acetonitrile (H2O/CH3CN) as the solvent, transforms a variety of primary, secondary and tertiary amines to the corresponding carbonyl compounds. In addition, this method was applied to the removal of a p-methoxylbenzyl (PMB) group from N-PMB protected amides.

Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases

In this study a diverse range of purified cobalt containing nitrile hydratases (NHases, EC 4.2.1.84) from Rhodopseudomonas palustris HaA2 (HaA2), Rhodopseudomonas palustris CGA009 (009), Sinorhizobium meliloti 1021 (1021), and Nitriliruptor alkaliphilus (iso2), were screened for the first time for their enantioselectivity towards a broad range of chiral nitriles. Enantiomeric ratios of >100 were found for the NHases from HaA2 and CGA009 on 2-phenylpropionitrile. In contrast, the Fe-containing NHase from the well-characterized Rhodococcus erythropolis AJ270 (AJ270) was practically aselective with a range of different α-phenylacetonitriles. In general, at least one bulky group in close proximity to the α-position of the chiral nitriles seemed to be necessary for enantioselectivity with all NHases tested. Nitrile groups attached to a quaternary carbon atom were only reluctantly accepted and showed no selectivity. Enantiomeric ratios of 80 and >100 for AJ270 and iso2, respectively, were found for the pharmaceutical intermediate naproxennitrile, and 3-(1-cyanoethyl)benzoic acid was hydrated to the corresponding amide by iso2 with an enantiomeric ratio of >100.

Nitrile hydratase activity of a recombinant nitrilase

Appreciable amounts of amide are formed in the course of nitrile hydrolysis in the presence of recombinant nitrilase from Pseudomonas fluorescens EBC 191, depending on the α-substituent and the reaction conditions. The ratio of the nitrilase and nitrile hydratase activities of the enzyme is profoundly influenced by the electronic and steric properties of the reactant. In general, amide formation increased when the α-substituent was electron-deficient; 2-chloro-2-phenylacetonitrile, for example, afforded 89% amide. We found, moreover, that (R)-mandelo-nitrile was hydrolysed with 11% of amide formation whereas 55% amide was formed from the (S)-enantiomer; a similar effect was found for the O-acetyl derivatives. A mechanism that accomodates our results is proposed.

Compounds for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof

Novel compounds of the pyridinium series useful for the management of diabetes and aging-related vascular and neurovascular complications, including kidney disease, nerve damage, atherosclerosis, retinopathy, inflammatory disorders, immunological disorders, oxidative stress, dermatological disorders and discoloration of teeth, by breaking preformed AGE, of the general formula I, or pharmaceutically acceptable salts thereof, wherein, R1, R2, R3, X and m are as defined in the specification. Also disclosed is a method for preparation of the compounds of general formula (I) and pharmaceutical composition containing one or more compounds as defined above as active ingredients. Also disclosed is a method of treatment of a diabetic patient by administering the compounds as defined above, either singly or in combination with drugs for antidiabetic therapy.

Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry

Novel compounds of the general formula STR1 and the pharmaceutically acceptable esters and acid addition salts thereof, wherein: R1, R2, R3, R4 and R5 are each independently hydrogen, lower alkyl, lower alkoxy, cyano, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl, N-optionally substituted alkylamido, except that when R1 is methyl, R4 is not methyl; or R2 and R3 together form --OCH2 O--; R6, R7, R8, R9 and R10 are each independently hydrogen, lower acyl, aminocarbonylmethyl, cyano, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl, di-lower alkyl amino; or R6 and R7 together form --CH=CH--CH=CH--; R7 and R8 together form --OCH2 O--; R11 and R12 are each independently hydrogen or lower alkyl; and W is oxygen or sulfur. These cardioselective compounds have calcium entry blockade properties and therefore are useful in therapy in the treatment of cardiovascular diseases, including arrhythmias, variant and exercise induced angina and myocardial infarction.

BENZODIOXANYL-HYDROXYETHYLENEAMINO-PIPERIDINYL ACETANILIDES, KETONES, ESTERS AND CARBAMATES WHICH EFFECT IMMUNITY AND CALCIUM ENTRY AND BETA-BLOCKADE

Novel compounds of the general formula: STR1 and the pharmaceutically acceptable acid addition salts thereof, wherein: R 1, R 2, R 3 and R 4 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl or lower alkyl sulfonyl;R 5 is hydrogen or lower alkyl;m is 0 or 1;W is alkylene,--CH=CH--,--O--, or--N(R 6)--, where R 6 is lower alkyl or hydrogen;n is 0 or 1; andQ is lower alkyl, cycloalkyl or optionally substituted phenyl. These compounds combine β-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including myocardial infarction, hypertension, arrhythmia and variant and exercise induced angina. The compounds are also useful in immunosuppressant therapy for immune diseases, such as rheumatoid arthritis.

Benzodioxanyl-hydroxyethylene-piperazinyl acetanilides which effect calcium entry and β-blockade

Novel compounds of the general formula: STR1 and the pharmaceutically acceptable esters and acid addition salts thereof, wherein: R1, R2, R3, R4, R5, R6, R7, R8 and R9 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl; or R2 and R3 together form --OCH2 O--; and R10 and R11 are each independently hydrogen or lower alkyl. These compounds combine β-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including hypertension, arrhythmias and variant and exercise induced angina.

Substituted mercapto acid amides and their use

Substituted mercapto acid amides are prepared, and are useful as immunoregulants for correcting an imbalance of immune homeostasis, particularly as immunostimulants in the treatment of autoimmune and immune deficient diseases and disorders.