13452-14-7

Basic information

• Product Name: 2-Methyl-1,3-benzoxazole-6-carboxylic acid
• Synonyms: 2-Methyl-6-benzoxazole carboxylic acid;2-METHYLBENZO[D]OXAZOLE-6-CARBOXYLIC ACID;2-Methyl-1,3-benzoxazole-6-carboxylic acid;2-Methylbenzoxazole-6-carboxylic Acid
• CAS NO: 13452-14-7
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• Mol File: 13452-14-7.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 353.462 °C at 760 mmHg
• Flash Point: 167.568 °C
• Appearance: /
• Density: 1.38 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: Room temperature.
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• CAS DataBase Reference: 2-Methyl-1,3-benzoxazole-6-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-1,3-benzoxazole-6-carboxylic acid(13452-14-7)
• EPA Substance Registry System: 2-Methyl-1,3-benzoxazole-6-carboxylic acid(13452-14-7)

Safety Data

• Hazardous Substances Data: 13452-14-7(Hazardous Substances Data)

Usage

Uses

2-Methyl-1,3-benzoxazole-6-carboxylic Acid is used in the synthesis of orexin 1 receptor antagonists, used in the treatment of obesity. Also used in the synthesis of novel benzoxazole amides as novel enhancers of HIV-1 protease inhibitors.

InChI:InChI=1/C9H7NO3/c1-5-10-7-3-2-6(9(11)12)4-8(7)13-5/h2-4H,1H3,(H,11,12)

Upstream product

• 63435-16-5 3-hydroxy-4-aminobenzoic acid methyl ester 
• 713-52-0 methyl 3-hydroxy-4-nitrobenzoate 
• 64-19-7 acetic acid 
• 2374-03-0 4-aminosalicylic acid 
• 1445-45-0 Trimethyl orthoacetate 
• 136663-23-5 methyl 2-methyl-1,3-benzoxazole-6-carboxylate 
• 6427-66-3 4-azidobenzoic acid 

Downstream Products

• 202195-57-1 2-methylbenzoxazole-6 carboxyl chloride 
• 5676-60-8 6-amino-2-methylbenzoxazole 
• 1393746-68-3 C₂₃H₂₉N₃O₃ 
• 792173-99-0 1-(2-methylbenzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea 

Relevant articles and documents

Hydrolytic instability of the important orexin 1 receptor antagonist SB-334867: Possible confounding effects on in vivo and in vitro studies

SB-334867 has been an important ligand for the study of the orexin 1 (OX1) receptor due to its high OX1/OX2 selectivity and bioavailability. This ligand however, contains a 2-methylbenzoxazole ring system which is known to undergo hydrolysis, particularly under acidic or basic conditions. The possibility that SB-334867 would be susceptible to significant hydrolysis was evaluated in various formulations and in the solid state. SB-334867 was found to be unstable under conditions commonly employed to prepare stock solutions for in vitro and in vivo studies. In addition, and most alarmingly, the hydrochloride salt of SB-334867 was found to quantitatively decompose to an OX1-inactive product even in the solid state. These findings combine to suggest that studies using SB-334867 (and any other 2-methylbenzoxazole-containing compound) should be performed with great care to avoid the confounding effects of the rapid hydrolytic decomposition of this susceptible structure.

GEMINAL SUBSTITUTED QUINUCLIDINE AMIDE COMPOUNDS AS AGONISTS OF ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel geminal substituted quinuclidine amide compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of α7- nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

Diaryl urea analogues of SB-334867 as orexin-1 receptor antagonists

As a part of our program to develop OX1-CB1 bivalent ligands, we required a better understanding of the basic structure-activity relationships (SARs) of orexin antagonists. A series of SB-334867 analogues were synthesized and evaluated in calcium mobilization assays. SAR results suggest that the 2-methylbenzoxazole moiety may be replaced with a disubstituted 4-aminophenyl group without loss of activity and an electron-deficient system is generally preferred at the 1,5-naphthyridine moiety for OX1 antagonist activity. In particular, substitution of larger potential linkers such as n-hexyl provided compound 33 with equivalent activity at the OX1 receptor compared to the lead compound SB-334867. These compounds should be of value in the development of ligands targeting the orexin-1 receptor and its potential heterodimers.