74409-42-0

Basic information

• Product Name: 2,3,5-Trimethylpyridine-1-Oxide
• Synonyms: 2,3,5-Trimethylpyridine-1-Oxide;2,3,5 -TRIMETHYLPYRIDINE N-OXIDE;2,3,5-Collidine N-Oxide;Pyridine,2,3,5-triMethyl-, 1-oxide;2,3,5-trimethyl-1-oxidopyridin-1-ium;Omeprazole Related Compound 4
• CAS NO: 74409-42-0
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.17904
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74409-42-0.mol

Chemical Properties

• Melting Point: 40-41 °C
• Boiling Point: 95-98 °C(Press: 0.00998 Torr)
• Appearance: /
• Density: 0.99±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 1.62±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2,3,5-Trimethylpyridine-1-Oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-Trimethylpyridine-1-Oxide(74409-42-0)
• EPA Substance Registry System: 2,3,5-Trimethylpyridine-1-Oxide(74409-42-0)

Safety Data

• Hazardous Substances Data: 74409-42-0(Hazardous Substances Data)

Usage

Chemical Properties

Light Brown Solid

Upstream product

• 695-98-7 2,3,5-trimethyl-pyridine 
• 75-09-2 dichloromethane 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 206990-64-9 acetic acid 3,5-dimethylpyridin-2-ylmethyl ester 
• 35392-67-7 3-methoxy-2-methyl-6-nitropyridine 1-oxide 
• 86604-79-7 2,3,5-trimethyl-4-nitropyridine N-oxide 
• 86604-80-0 4-methoxy-2,3,5-trimethylpyridine 1-oxide 
• 70580-28-8 C₈H₁₁NO*ClH 
• 142885-96-9 2-chloromethyl-4-chloro-3,5-dimethylpyridine 
• 153476-69-8 2-(chloromethyl)-3,5-dimethylpyridine 
• 73590-93-9 2-chloromethyl-3,5-dimethylpyridine hydrochloride 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 
• 91219-90-8 (4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl acetate 
• 86604-78-6 (4-methoxy-3,5-dimethylpyridin-2-yl)methanol 
• 202932-05-6 2-hydroxymethyl-3,5-dimethylpyridine 
• 943315-18-2 2-bromomethyl-4-cyano-3,5-dimethylpyridine 
• 149082-03-1 2-hydroxymethyl-3,5-dimethyl-4-nitropyridine 

Relevant articles and documents

An industrialized method for preparing nitro mediums of proton pump inhibitors

The present invention discloses an industrial method for preparing a proton pump inhibitor intermediate nitro group, belongs to the field of chemical synthesis technology, the method comprising preparing nitrogen oxides and preparing nitro groups; the preparation of nitrogen oxides, using pyridine derivatives as starting materials, reacting with oxidants under the action of a catalyst to generate nitrogen oxides; the preparation of nitro groups, after dissolving nitrogen oxides using organic solvents, using microchannel reaction technology, using fuming nitric acid as a nitrification reagent, nitrification reaction, The method of the present invention can reduce the generation of reaction impurities, shorten the reaction time, improve product quality, and greatly improve the continuity and safety of industrial production.

Synthesis method of 4-methoxy-2, 3, 5-trimethyl-pyridine nitrogen oxide

The invention discloses a synthesis method of 4-methoxy-2, 3, 5-trimethyl-pyridine nitrogen oxide, which comprises the following steps: S1, carrying out bromination reaction and methoxy substitution on 2, 3, 5-trimethylpyridine-N-oxide to obtain 4-bromine-2, 3, 5-trimethyl-pyridine nitrogen oxide; and S2, carrying out a sodium methoxide substitution reaction on the 4-bromo-2, 3, 5-trimethyl-pyridine nitrogen oxide to generate an important intermediate 4-methoxy-2, 3, 5-trimethyl-pyridine nitrogen oxide of omeprazole. According to the method, bromate and bromide which are mild bromination reaction conditions are adopted in the process route, then the bromate intermediate is used for carrying out methoxy substitution reaction, and the whole process is simple in design, mild in reaction condition and easy and convenient to operate.

Synthesis and characterization of one impurity in esomeprazole, an antiulcerative drug

During drug synthesis, control of impurities is very important to get high-qualified drugs. A number of studies have devoted to synthesize the impurities and study the structures to support the method of purification. In this paper, we first synthesize one impurity in esomeprazole, rel-2-[[(3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-6-methoxy-1H-benzimidazole, with readily available raw materials, simple operation procedures and relatively mild reaction. Besides, we characterized its structure by MS, IR, 1H-NMR and HPLC analyses. The purity of target compound is as high as 99.58%, which can be used as the reference substance of the impurities of esomeprazole.

4-nitro-2,3,5-trimethylpyridine-N-oxide preparation method

The invention belongs to the field of preparation of chemical industry intermediates, and particularly relates to a 4-nitro-2,3,5-trimethylpyridine-N-oxide preparation method, which comprises: obtaining a 2,3,5-trimethylpyridine-N-oxide, and obtaining a 4-nitro-2,3,5-trimethylpyridine-N-oxide. According to the present invention, the preparation method has characteristics of high yield, low raw material cost, simple treatment and good product quality, and is suitable for industrial production.

A chemical chaperone-based drug candidate is effective in a mouse model of amyotrophic lateral sclerosis (ALS)

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the selective death of motor neurons and skeletal muscle atrophy. The majority of ALS cases are acquired spontaneously, with inherited disease accounting for only 10 % of all cases. Recent studies provide compelling evidence that aggregates of misfolded proteins underlie both types of ALS. Small molecules such as artificial chaperones can prevent or even reverse the aggregation of proteins associated with various human diseases. However, their very high active concentration (micromolar range) severely limits their utility as drugs. We synthesized several ester and amide derivatives of chemical chaperones. The lead compound 14, 3-((5-((4,6-dimethylpyridin-2-yl)methoxy)-5-oxopentanoyl)oxy)-N,N-dimethylpropan-1-amine oxide shows, in the micromolar concentration range, both neuronal and astrocyte protective effects in vitro; at daily doses of 10 mg kg-1 14 improved the neurological functions and delayed body weight loss in ALS mice. Members of this new chemical chaperone derivative class are strong candidates for the development of new drugs for ALS patients.

Discovery and crystallography of bicyclic arylaminoazines as potent inhibitors of HIV-1 reverse transcriptase

Non-nucleoside inhibitors of HIV-1 reverse transcriptase (HIV-RT) are reported that incorporate a 7-indolizinylamino or 2-naphthylamino substituent on a pyrimidine or 1,3,5-triazine core. The most potent compounds show below 10 nanomolar activity towards wild-type HIV-1 and variants bearing Tyr181Cys and Lys103Asn/Tyr181Cys resistance mutations. The compounds also feature good aqueous solubility. Crystal structures for two complexes enhance the analysis of the structure-activity data.

5-lipoxygenase-activating protein (FLAP) inhibitors. Part 4: Development of 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin- 2-ylmethoxy)-1 H -indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor

The potent 5-lipoxygenase-activating protein (FLAP) inhibitor 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2- ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid 11cc is described (AM803, now GSK2190915). Building upon AM103 (1) (Hutchinson et al. J. Med Chem.2009, 52, 5803-5815; Stock et al. Bioorg. Med. Chem. Lett. 2010, 20, 213-217; Stock et al. Bioorg. Med. Chem. Lett.2010, 20, 4598-4601), SAR studies centering around the pyridine moiety led to the discovery of compounds that exhibit significantly increased potency in a human whole blood assay measuring LTB4 inhibition with longer drug preincubation times (15 min vs 5 h). Further studies identified 11cc with a potency of 2.9 nM in FLAP binding, an IC50 of 76 nM for inhibition of LTB4 in human blood (5 h incubation) and excellent preclinical toxicology and pharmacokinetics in rat and dog. 11cc also demonstrated an extended pharmacodynamic effect in a rodent bronchoalveolar lavage (BAL) model. This compound has successfully completed phase 1 clinical studies in healthy volunteers and is currently undergoing phase 2 trials in asthmatic patients.

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.

Synthesis and characterization of metabolites and potential impurities of the antiulcerative drug tenatoprazole

Tenatoprazole (Ulsacare) is a recently developed antiulcerative drug used for the treatment of both erosive and nonerosive gastroesophageal reflux disease. During the bulk synthesis of tenatoprazole, we have observed four impurities (tenatoprazole N-oxide, tenatoprazole sulfone N-oxide, N-methyl tenatoprazole, and desmethoxy tenatoprazole) and two metabolites (tenatoprazole sulfide and tenatoprazole sulfone). The present work describes the synthesis and characterization of these impurities. Copyright Taylor & Francis Group, LLC.