128073-03-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Pyridinecarbonyl chloride, 5-chloro(9CI) is used as a reactive intermediate for the synthesis of various pharmaceuticals and medications. Its unique structure and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
In the agrochemical industry, 2-Pyridinecarbonyl chloride, 5-chloro(9CI) is utilized in the production of various agrochemicals. Its role as a building block allows for the creation of compounds that can be used in pest control and crop protection.
Used in Dye and Pigment Manufacturing:
2-Pyridinecarbonyl chloride, 5-chloro(9CI) is also employed in the manufacturing of dyes and pigments. Its chemical properties contribute to the color and stability of these products, making it an important component in the dye and pigment industry.
Used in Organic Synthesis:
As a versatile building block, 2-Pyridinecarbonyl chloride, 5-chloro(9CI) is widely used in organic synthesis for the creation of a variety of chemical compounds. Its reactivity and structural features make it a valuable tool in the synthesis of complex organic molecules.

Upstream product

• 86873-60-1 5-chloropicolinic acid 
• 21684-59-3 ethyl 6-methylnicotinate 
• 197079-25-7 6-methylpyridine-3-carbohydrazide 
• 247077-42-5 (6-methyl-[3]pyridyl)-carbamic acid ethyl ester 
• 70788-54-4 2,3,4-trichloro-6-(trichloromethyl)pyridine 
• 858844-85-6 1,3-bis(6-methylpyridin-3-yl)urea 
• 64038-04-6 6-methyl-nicotinoyl azide 
• 6960-22-1 6-methylnicotinamide 
• 72093-07-3 2-methyl-5-chloropyridine 
• 80287-53-2 5-Amino-2-methylpyridine 
• 1199-48-0 4,5-dichloro-2-(trichloromethyl)pyridine 

Downstream Products

• 132308-19-1 methyl 5-chloropyridine-2-carboxylate 
• 1113049-94-7 C₂₆H₂₁ClF₄N₆O₄ 
• 1113050-22-8 C₂₇H₂₁ClF₄N₆O₅ 
• 1271949-52-0 5-chloro-pyridine-2-carboxylic acid (3-acetyl-4-fluoro-phenyl)-amide 
• 935999-02-3 5-chloro-pyridine-2-carboxylic acid [3-((S)-2-amino-4-methyl-5,6-dihydro-4H-[1,3]thiazin-4-yl)-4-fluoro-phenyl]-amide 
• 1271949-54-2 5-chloro-pyridine-2-carboxylic acid [4-fluoro-3-(1-hydroxy-1-methyl-allyl)-phenyl]-amide 
• 1271949-56-4 5-chloro-pyridine-2-carboxylic acid [3-((E)-3-carbamimidoylsulfanyl-1-methyl-propenyl)-4-fluoro-phenyl]-amide hydrochloride 
• 1271948-76-5 (S)-N-(3-(2-amino-4-methyl-5,6-dihydro-4H-1,3-thiazin-4-yl)-4-fluorophenyl)-5-chloropicolinamide 
• 1271949-32-6 5-chloro-pyridine-2-carboxylic acid [3-((R)-2-amino-4-methyl-5,6-dihydro-4H-[1,3]thiazin-4-yl)-4-fluoro-phenyl]-amide 
• 103878-84-8 lazabemide 
• 342601-76-7 5-chloro-N-methoxy-N-methylpicolinamide 
• 10177-24-9 5-chloro-pyridin-2-ylmethyl chloride 
• 929214-89-1 methyl 2-{[(5-chloropyridin-2-yl)carbonyl]amino}-4-methylbenzoate 
• 1163694-03-8 C₂₆H₂₂ClF₃N₆O₅ 

Relevant academic research and scientific papers

Design and Discovery of Novel Antifungal Quinoline Derivatives with Acylhydrazide as a Promising Pharmacophore

Inspired by natural 2-quinolinecarboxylic acid derivatives, a series of quinoline compounds containing acylhydrazine, acylhydrazone, sulfonylhydrazine, oxadiazole, thiadiazole, or triazole moieties were synthesized and evaluated for their fungicidal activity. Most of these compounds exhibited excellent fungicidal activity in vitro. Significantly, compound 2e displayed the superior in vitro antifungal activity against Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea, and Fusarium graminearum with the EC50 values of 0.39, 0.46, 0.19, and 0.18 μg/mL, respectively, and were more potent than those of carbendazim (EC50, 0.68, 0.14, >100, and 0.65 μg/mL, respectively). Moreover, compound 2e could inhibit spore germination of F. graminearum. Preliminary mechanistic studies showed that compound 2e could cause abnormal morphology of cell walls and vacuoles, loss of mitochondrion, increases in membrane permeability, and release of cellular contents. These results indicate that compound 2e displayed superior fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

Atroposelective Synthesis of Axially Chiral Styrenes via an Asymmetric C–H Functionalization Strategy

Axially chiral styrenes, which exhibit a chiral axis between a substituted alkene and an aromatic ring, have been largely overlooked. The hurdle is the lower barriers to rotation compared with that of their biaryl counterparts, rendering their asymmetric synthesis more difficult. We report herein the highly atroposelective synthesis via a C?H functionalization strategy of axially chiral styrenes with an open-chained alkene. Various axially chiral styrenes were produced by Pd(II)-catalyzed C?H alkenylation and alkynylation in good yields (up to 99%) and enantioselectivities (up to 99% ee) by using L-pyroglutamic acid as an inexpensive chiral ligand. The potent application of the styrene atropisomers is demonstrated by a Co(III)-catalyzed enantioselective C?H amidation of ferrocene with axially chiral styrene-type acid as chiral ligand. Experimental and computational studies were conducted to elucidate the reaction mechanism. The chiral induction model of the enantioselectivity-determining C?H bond activation step was also provided based on DFT calculations. Atropisomerism, which stems from the hindered rotation around a chiral axis, is widely present in natural products, pharmaceuticals, and chiral catalysts or ligands. In contrast to the well-investigated biaryl atropisomers, the asymmetric synthesis of axially chiral styrenes bearing a chiral axis between an alkene and an aromatic ring remains a significant challenge. Here, we report a highly atroposelective synthesis of styrene atropisomers with open-chained alkene by asymmetric C?H functionalization by using available L-pyroglutamic acid as a chiral ligand. This strategy enables rapid access to a broad range of enantio-enriched axially chiral styrenes under mild conditions in an atom- and step-economical manner. The resulting axially chiral styrenes are important precursors for further elaborations, including the transformation into axially chiral styrene-type acids, which were demonstrated to be efficient chiral ligands in Co(III)-catalyzed enantioselective C?H amidation reactions. An asymmetric C–H functionalization strategy with L-pGlu-OH as chiral ligand has been developed for the atroposelective synthesis of styrene atropisomers with open-chained alkene. The strategy allows quick access to a wide range of enantio-enriched axially chiral styrenes in high yields and enantioselectivities. The axially chiral styrene-derived chiral acids have been demonstrated to be an efficient type of chiral ligands in Co(III)-catalyzed enantioselective C?H amidation reactions.

Synthetic method of novel monoamine oxidase inhibitor (malabemide)

The invention discloses a synthetic method of a novel monoamine oxidase inhibitor (malabemide). According to the synthetic method, 5-chloro-2-pyridine carboxylic acid is taken as the primary raw material, after acyl-chlorination reactions, 5-chloro-2-pyridine formyl chloride is generated; then after amidation reactions, 5-chloro-N-(2-hydroxyethyl)-2-pyridine formyl chloride is generated, and finally 5-chloro-N-(2-hydroxyethyl)-2-pyridine formyl chloride and morpholine carry out condensation reactions to generate malabemide. Ethanolamine, 5-chloro-2-pyridine carboxylic acid, and morpholine aretaken as the main raw materials to prepare the novel monoamine oxidase inhibitor (malabemide); and the raw materials are easily available. The synthetic method has the advantages of simple operation,high product purity, and high yield, and is suitable for industrial production.

Rh-Catalyzed Annulative Insertion of Terminal Olefin onto Pyridines via a C-H Activation Strategy Using Ethenesulfonyl Fluoride as Ethylene Provider

A Rh(III)-catalyzed annulative insertion of ethylene onto picolinamides was achieved, providing a portal to a class of unique pyridine-containing molecules bearing a terminal olefin moiety for diversification. Application of this method for modification of Sorafenib was also accomplished.

New compound Malabemide, preparation method and uses thereof

The invention discloses a new compound Malabemide with a molecule formula represented by a formula h, a preparation method and pharmaceutical applications thereof, wherein ethanolamine and 5-chloro-2-pyridinecarboxylic acid are used as starting raw materials, corresponding intermediates 2-bromoethylamine hydrobromide and 5-chloro-2-pyridinecarbonyl chloride are respectively synthesized, and are subjected to a reaction to generate 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide, and the 5-chloro-N-(2-bromoethyl)-2-pyridinecarboxamide and morpholine are subjected to condensation to generate Malabemide h. According to the present invention, the preparation method has characteristics of easily available raw materials, simple operation, good product purity and high yield, and is suitable for industrial production. The formula h is defined in the specification.

Design, synthesis and biological evaluation of lazabemide derivatives as inhibitors of monoamine oxidase

In the studied a series novel of lazabemide derivatives were designed, synthesized and evaluated as inhibitors of monoamine oxidase (MAO-A or MAO-B). These compounds used lazabemide as the lead compound, and the chemistry structures were modified by used the bioisostere and modification of compound with alkyl principle. The two types of inhibitors (inhibition of MAO-A and inhibition of MAO-B) were screened by inhibition activity of MAO. In vitro experiments showed that compounds 3a, 3d and 3f had intensity inhibition the biological activity of MAO-A, while compounds 3i and 3m had intensity inhibition the biological activity of MAO-B. It could be seen from the data of inhibition activity experiments in vitro, that the compound 3d was IC50 = 3.12 ± 0.05 μmol/mL of MAO-A and compound 3m was IC50 = 5.04 ± 0.06 μmol/mL. In vivo inhibition activity experiments were conducted to evaluate the inhibitory activity of compounds 3a, 3d, 3f, 3i and 3m by detecting the contents of 5-HT, NE, DA and activity of MAO-A and MAO-B in plasma and brain tissue. In vivo inhibition activity evaluation results showed that the compounds 3a, 3d, 3f, 3i and 3m had increased the contents of 5-HT, NE and DA in plasma and brain tissues. Meanwhile, the determination results activity of MAO in plasma and brain tissue showed that the compounds 3a, 3d, and 3f had a significant inhibitory effect on the activity of MAO-A, while the compounds 3i and 3m showed inhibitory effect on the activity of MAO-B. This study provided a new inhibitors for inhibiting of MAO activity.

BACE1 INHIBITORS

The present invention provides a compound of formula I, having BACE1 inhibitory activity, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances. The active compounds of the present invention are useful in the therapeutic and/or prophylactic treatment of e.g. Alzheimer's disease.

Discovery and Optimization of Chromeno[2,3-c]pyrrol-9(2H)-ones as Novel Selective and Orally Bioavailable Phosphodiesterase 5 Inhibitors for the Treatment of Pulmonary Arterial Hypertension

Phosphodiesterase 5 (PDE5) inhibitors have been used as clinical agents to treat erectile dysfunction and pulmonary arterial hypertension (PAH). Herein, we detail the discovery of a novel series of chromeno[2,3-c]pyrrol-9(2H)-one derivatives as selective and orally bioavailable inhibitors against phosphodiesterase 5. Medicinal chemistry optimization resulted in 2, which exhibits a desirable inhibitory potency of 5.6 nM with remarkable selectivity as well as excellent pharmacokinetic properties and an oral bioavailability of 63.4%. In addition, oral administration of 2 at a dose of 5.0 mg/kg caused better pharmacodynamics effects on both mPAP (mean pulmonary artery pressure) and RVHI (index of right ventricle hypertrophy) than sildenafil citrate at a dose of 10.0 mg/kg. These activities along with its reasonable druglike properties, such as human liver microsomal stability, cytochrome inhibition, hERG inhibition, and pharmacological safety, indicate that 2 is a potential candidate for the treatment of PAH.

BACE1 INHIBITORS

The present invention provides a compound of formula I, having BACE1 inhibitory activity, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances. The active compounds of the present invention are useful in the therapeutic and/or prophylactic treatment of e.g. Alzheimer's disease.

Iridium(III)-Catalyzed Regioselective Intermolecular Unactivated Secondary Csp3?H Bond Amidation

For the first time, a highly regioselective intermolecular sulfonylamidation unactivated secondary Csp3?H bond has been achieved using IrIIIcatalysts. The introduced N,N’-bichelating ligand plays a crucial role in enabling iridium–nitrene insertion into a secondary Csp3?H bond via an outer-sphere pathway. Mechanistic studies and density functional theory (DFT) calculations demonstrated that a two-electron concerted nitrene insertion was involved in this Csp3?H amidation process. This method tolerates a broad range of linear and branched-chain N-alkylamides, and provides efficient access to diverse γ-sulfonamido-substituted aliphatic amines.