109371-20-2

Basic information

• Product Name: 4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE
• Synonyms: 4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE;4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-N-OXIDE;4-CHLORO-2,3,5-TRIMETHYLPYRIDINIUM-1-OLATE;2,3,5-TRIMETHYL 4-CHLORO PYRIDINE N-OXIDE;Pyridine,4-chloro-2,3,5-triMethyl-, 1-oxide;Pyridine,4-chloro-2,3,5-triMethyl-;4-chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium
• CAS NO: 109371-20-2
• Molecular Formula: C₈H₁₀ClNO
• Molecular Weight: 171.62
• Mol File: 109371-20-2.mol

Chemical Properties

• Melting Point: 148 °C
• Boiling Point: 347°C at 760 mmHg
• Flash Point: 163.7°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.000111mmHg at 25°C
• Refractive Index: 1.532
• PKA: 1.52±0.10(Predicted)
• CAS DataBase Reference: 4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE(109371-20-2)
• EPA Substance Registry System: 4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE(109371-20-2)

Safety Data

• Hazardous Substances Data: 109371-20-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE is used as a building block for the synthesis of various medications due to its versatile chemical structure and reactivity. It plays a crucial role in the development of new drugs and the improvement of existing ones.
Used in Organic Synthesis:
4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE is utilized as an intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds with diverse applications.
Used in Chemical Research:
As a pyridine derivative with unique structural features, 4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE is employed in chemical research to explore its properties, reactivity, and potential applications in various chemical processes.
Safety Considerations:
Due to its potentially hazardous nature, 4-CHLORO-2,3,5-TRIMETHYLPYRIDINE-1-OXIDE must be handled and stored with care to ensure the safety of individuals and the environment. Proper safety measures, including the use of personal protective equipment and adherence to storage guidelines, are essential when working with this compound.

InChI:InChI=1/C8H10ClNO/c1-5-4-10(11)7(3)6(2)8(5)9/h4H,1-3H3

Upstream product

• 695-98-7 2,3,5-trimethyl-pyridine 
• 109371-16-6 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 
• 109371-17-7 2,4-dichloro-3,5,6-trimethylpyridine 
• 86604-79-7 2,3,5-trimethyl-4-nitropyridine N-oxide 
• 109371-18-8 4-chloro-2,3,5-trimethylpyridine 

Downstream Products

• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 96300-88-8 2-Hydroxymethyl-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 91219-90-8 (4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl acetate 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 142885-96-9 2-chloromethyl-4-chloro-3,5-dimethylpyridine 
• 913696-26-1 4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-2,3,5-trimethylpyridine1-oxide 
• 109371-18-8 4-chloro-2,3,5-trimethylpyridine 
• 113618-20-5 4-(2,3,5-Trimethyl-pyridin-4-yl)-morpholine 

Relevant articles and documents

BENZIMIDAZOLE COMPOUND HAVING GASTRIC ACID SECRETION INHIBITORY ACTIVITY

The present invention provides a compound that has superior gastric acid secretion inhibitory action, ample long-lasting gastric acid secretion inhibitory action, and is able to maintain intragastric pH at a high level for an extended period of time, making it useful as a therapeutic or prophylactic agent for diseases or symptoms caused by gastric acid, as well as an active form of this compound (form to which the compound is converted in the body following administration thereof) in the form of a compound represented by general formula (1 a) (wherein R2 represents a group represented by formula (I) or the like, and R1, R3, W1 and X- are as defined in the description).

SALT OF SULFINYLBENZIMIDAZOLE COMPOUND, AND CRYSTAL AND AMORPHOUS FORM THEREOF

Salts of 2-[({4-[(2.2-dimethyl-1,3-dioxan-5-yl)methoxy]-3,5-dimethylpyridin-2-yl}methyl)sulfinyl]-1H-benzimidazole and their crystalline and amorphous forms.

PROCESS FOR THE PRODUCTION OF 2- [ [4- T (2, 2-DIMETHYL-1, 3-DIOXAN-5-YL) METHOXY] PYRIDIN-2-YL] METHYLTHIO] -1H-BENZIMIDAZOLE

It is an object of the present invention to provide a process for the production on an industrial scale of a compound (1) or a salt thereof. There is provided a process for the production of compound (1) represented by the formula or a salt thereof: (wherein R1 and R3 independently represents a hydrogen atom or a methyl group), the process comprising the steps of: (a) reacting together a compound (3T) represented by the formula: (wherein X1 represents a leaving group, and R1 and R3 are defined as above) and (2,2-dimethyl-1,3-dioxan-5-yl)methanol represented by the formula or a salt thereof: so as to produce a compound (2T) represented by the formula (wherein R1 and R3 are defined as above); and (b) reacting the compound represented by above formula (2T) with an oxidizing agent.

STABILIZED COMPOSITION

It is intended to provide a pharmaceutical composition which contains a proton pump inhibitor and is stable even if it is stored for a long time. It is also intended to provide a pharmaceutical composition which contains a proton pump inhibitor susceptible to acid, and does not dissolve in the stomach but dissolves in the intestine to release a primary drug product promptly. The object could be achieved by the pharmaceutical composition characterized in that a layer containing a proton pump inhibitor and ethyl cellulose, a layer containing an enteric polymer, and if necessary an intermediate layer composed of one or more layers are formed on a pharmacologically inactive core substance. The intermediate layer is composed of a water-insoluble polymer, a water-soluble polymer, a lubricant and the like.

Benzimidazole compound

An object of the present invention is to provide a novel chemical compound useful as a therapeutic or prophylactic agent for acid-related diseases, having an excellent inhibitory effect against gastric acid secretion, an excellent effect of maintaining the inhibitory effect against gastric acid secretion, thereby maintaining intragastric pH high for a long time, and having more safety and appropriate physicochemical stability. Provided is a compound represented by where R1 and R3 may be the same or different and each represent a hydrogen atom or a C1-C6 alkyl group; R2 represents (5,5-dimethyl-1,3-dioxan-2-yl)methoxy group, 5,7-dioxaspiro[2.5]oct-6-ylmethoxy group, 1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy group, or (2,2-dimethyl-1,3-dioxan-5-yl)methoxy group; R4, R5, R6 and R7 represent a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group or C1-C6 haloalkoxy group; and W1 represents a single bond, methylene or ethylene group, a salt thereof or a solvate of these.

A process for the preparation of omeprazol

The process starts by reacting 2,3,5 trimethylpyridine with hydrogen peroxide in the presence of catalysts, giving new reactive ionic species allowing the number of required steps to be substantially reduced. In the final important step, oxidation to omeprazol, there are used new salts of 5-methoxy-2-((3,5-dimethyl-4-methoxy-2-pyridine)methylthio)-1H-benzimidazole which, as the oxidation evolves, precipitate the omeprazol. The new oxidation method avoids superoxidations, provide for faster oxidation, high purity and yields of over 90%.

Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.

A new synthesis of 4-methoxy-2,3,5-trimethylpyridine (2), an important building block for the preparation of gastric-acid inhibiting compounds, is described. Condensation of ethyl 3-amino-2-methyl-2-butenoate (3) and diethyl 2-methylmalonate (4) gives 4-hydroxy-3,5,6-trimethyl-2(1H)-pyridone 5. Reaction of 5 with phosphoryl chloride affords 2,4-dichloro-3,5,6-trimethylpyridine (9a), which, upon hydrogenolysis with palladium on charcoal, gives 2,3,5-trimethylpyridine (10). However, selective hydrogenolysis in acidic solution yields 4-chloro-2-3-5-trimethylpyridine (11). Substitution of the chlorine in 11 with methoxide ion gives 4-methoxy-2,3,5-trimethylpyridine (2), which can be oxidized to the corresponding N-oxide (13). This constitutes a new and efficient route to compound 2 in an overall yield of 43%.

2,4-dichloro-3,5,6-trimethylpyridine

A method for the preparation of 2,3,5-trimethylpyridine and some of its derivatives.

SYNTHESIS OF STERICALLY HINDERED 4-DIALKYLAMINO PYRIDINES

The synthesis of sterically hindered 4-dialkylamino pyridines from a 2,3,5-trisubstituted 4-nitropyridine-N-oxide was found to proceed via a different reaction sequence under acidic and basic conditions.