93271-59-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-4-methylpyridine-3-carbonitrile is used as a key intermediate for the synthesis of various drugs. Its unique structure and functional groups make it a valuable building block in the development of new pharmaceuticals, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Hydroxy-4-methylpyridine-3-carbonitrile is utilized as a precursor in the production of pesticides. Its reactivity and functional groups enable the creation of effective agrochemicals, enhancing crop protection and contributing to sustainable agriculture.
Used in Chemical Research and Industrial Processes:
2-Hydroxy-4-methylpyridine-3-carbonitrile also serves as a chelating agent and metal complexation reagent in chemical research and industrial processes. Its ability to form stable complexes with metal ions makes it a useful tool in various chemical applications, including catalysis and the synthesis of inorganic compounds.
Overall, 2-Hydroxy-4-methylpyridine-3-carbonitrile is a versatile and essential compound in the fields of pharmaceuticals, agrochemicals, and chemical research, playing a significant role in the development and production of various products.

InChI:InChI=1/C7H6N2O/c1-5-2-3-9-7(10)6(5)4-8/h2-3H,1H3,(H,9,10)

Upstream product

• 65996-11-4 1-carbethoxy-1-cyano-2-methyl-4-dimethylamino-1,4-butadiene 
• 759-58-0 ethyl isopropylidenecyanoacetate 
• 410547-38-5 1,1-dicyano-4-methoxy-2-methyl-1,3-butadiene 
• 410547-37-4 4,4-dicyano-3-methyl-3-butenal dimethyl acetal 
• 1025080-30-1 [(2E)-3-methoxy-1-methylprop-2-en-1-ylidene]malononitrile 
• 71493-76-0 2-amino-4-methylpyridine-3-carbonitrile 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 
• 107-91-5 cyanoacetic acid amide 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 109-77-3 malononitrile 
• 93271-58-0 2-isopropylidenecyanoacetamide 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 

Downstream Products

• 149379-71-5 2-methoxy-4-methylpyridine-3-carbonitrile 
• 65169-38-2 2-chloro-4-methyl-3-pyridinecarbonitrile 
• 57839-80-2 3-Acetyl-4-methyl-2(1H)-pyridon 

Relevant academic research and scientific papers

Pyrrole-3-formamide compound as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and relates to a pyrrole-3-formamide compound as well as a preparation method and application thereof, in particular to a pyrrole-3-formamidecompound shown as a formula (I) or (II) and a pharmaceutically-acceptable salt thereof, wherein R to R and X are defined in the claims and description. The preparation of the compound mainly comprises performing Knorr pyrrole synthesis, Hantzsch pyrrole synthesis, decarboxylation, alkylation, hydrolysis, condensation, cyclization and reduction on ethyl acetoacetate or tert-butyl acetoacetate serving as the raw material. The pyrrole-3-formamide compound and the pharmaceutically-acceptable salt thereof have good treatment effects on tumors, and can be applied to the preparation of anti-tumor drugs. (The formulas (I) and (II) are shown in the description).

Antitumor compound used as AXL inhibitor and application of antitumor compound

The invention discloses a compound shown in a general formula (I) or pharmaceutically acceptable salt of the compound and preparation methods of the compound and the salt, and further discloses pharmaceutical composition containing the compound and an application of the compound and the pharmaceutical composition in preparation of an AXL inhibitory drug. The AXL inhibitory drug is used for treating tumor, nephropathy, immune system disease or circulatory system disease.

Polypharmacological profile of 1,2-dihydro-2-oxo-pyridine-3-carboxamides in the endocannabinoid system

The endocannabinoid system (ECS) represents one of the major neuromodulatory systems involved in different physiological and pathological processes. Multi-target compounds exert their activities by acting via multiple mechanisms of action and represent a promising pharmacological modulation of the ECS. In this work we report 4-substituted and 4,5-disubstituted 1,2-dihydro-2-oxo-pyridine-3-carboxamide derivatives with a broad spectrum of affinity and functional activity towards both cannabinoid receptors and additional effects on the main components of the ECS. In particular compound B3 showed high affinity for CB1R (Ki = 23.1 nM, partial agonist) and CB2R (Ki = 6.9 nM, inverse agonist) and also significant inhibitory activity (IC50 = 70 nM) on FAAH with moderate inhibition of ABHD12 (IC50 = 2.5 μΜ). Compounds B4, B5 and B6 that act as full agonists at CB1R and as partial agonists (B5 and B6) or antagonist (B4) at CB2R, exhibited an additional multi-target property by inhibiting anandamide uptake with sub-micromolar IC50 values (0.28–0.62 μΜ). The best derivatives showed cytotoxic activity on U937 lymphoblastoid cells. Finally, molecular docking analysis carried out on the three-dimensional structures of CB1R and CB2R and of FAAH allowed to rationalize the structure-activity relationships of this series of compounds.

Improved synthesis of 2-chloro-3-amino-4-methylpyridine

2-Chloro-3-amino-4-methylpyridine (), a key intermediate in the synthesis of nervirapine, was prepared from 2-cyanoacetamide and 4,4-dimethoxyl-2-butanone via condensation, cyclization, one-pot reaction of chlorination and hydrolysis, and Hofmann reaction. Utilization of the quadratic orthogonal test resulted in a high yield (62.1%) of the whole process.

A concise synthesis of 2-chloro-3-amino-4-methylpyridine

An improved and commercially valuable process is developed for the scalable synthesis of 2-chloro-3-amino-4-methylpyridine (CAPIC), a key intermediate of Nevirapine. The synthesis was accomplished in four steps, featuring condensation starting from 4,4-dimethoxyl-2-butanone and cyanoacetamide with ammonium acetate and acetic acid as catalysts. The total yield of the process is 62.1%. The pure CAPIC sample was confirmed with FTIR, 1H NMR, and 13C NMR spectra.

CASPASE INHIBITORS BASED ON PYRIDONE SCAFFOLD

The present invention relates to a pyridone derivative which can be used as a caspase inhibitor, process for the preparation thereof, and pharmaceutical composition for inhibiting caspase comprising the same.

CASPASE INHIBITORS BASED ON PYRIDAZINONE SCAFFOLD

The present invention relates to a pyridone derivative which can be used as a caspase inhibitor, process for the preparation thereof, and pharmaceutical composition for inhibiting caspase comprising the same.

BACTERICIDE COMPOSITION AND METHOD OF CONTROLLING PLANT DISEASE

It is to provide a fungicidal composition having stable and high fungicidal effects against cultivated crops infected with plant diseases resulting from plant diseases. A fungicidal composition containing as active ingredients (a) a benzoylpyridine derivative represented by the formula (I) or its salt: (wherein X is a halogen atom, a nitro group, a substitutable hydrocarbon group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group, a hydroxyl group, a substitutable alkylthio group, a cyano group, a carboxyl group which may be esterified or amidated, or a substitutable amino group, n is 1, 2, 3 or 4; R1 is a substitutable alkyl group, R2' is a substitutable alkyl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable cycloalkoxy group or a hydroxyl group, p is 1, 2 or 3, and R2" is a substitutable alkoxy group or a hydroxyl group, provided that at least two of R2' and R2" may form a condensed ring containing an oxygen atom) and (b) at least one another fungicide.

SYNTHESIS OF 3-AMINO-2-CHLORO-4-METHYLPYRIDINE FROM MALONONITRILE AND ACETONE

A method for making 3-amino-2-chloro-4-methylpyridine from malononitrile, as depicted in the following reaction scheme.

Synthesis of 3-amino-2-chloro-4-methylpyridine from malononitrile and acetone

A method for making 3-amino-2-chloro-4-methylpyridine from malononitrile, as depicted in the following reaction scheme.