16727-43-8 | 2,6-Dimethoxypyridine-3-carboxylic acid

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$10.00	$7.00
250mg	95%	in stock	$23.00	$16.00
1g	95%	in stock	$57.00	$40.00
5g	95%	in stock	$165.00	$115.00
10g	95%	in stock	$297.00	$208.00
25g	95%	in stock	$572.00	$400.00
100g	95%	in stock	$1,878.00	$1,315.00

Description

• Catalog Number: AB43720
• Chemical Name: 2,6-Dimethoxypyridine-3-carboxylic acid
• CAS Number: 16727-43-8
• Molecular Formula: C8H9NO4
• Molecular Weight: 183.1614
• MDL Number: MFCD00075582
• SMILES: COc1nc(OC)ccc1C(=O)O

Computed Properties

• Complexity: 185
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 3
• XLogP3: 1

Upstream Synthesis Route

The synthesis of 2,6-Dimethoxypyridine-3-carboxylic acid can be achieved through the following upstream route:

1. **Start with Nicotinic acid (pyridine-3-carboxylic acid)**: Nicotinic acid is a readily accessible starting material which serves as the pyridine scaffold.

2. **Methylation of the pyridine ring**: Typically, dimethyl sulfate or methyl iodide can be used to introduce the methoxy groups at the 2 and 6 positions on the pyridine ring, sometimes with the aid of a base such as potassium carbonate (K2CO3) in a suitable solvent like acetone or DMF. This would afford 2,6-dimethoxypyridine-3-carboxylic acid directly, given the steric hindrance is not too high for methylation at the 6-position.

3. **Protection of the carboxylic group**: In some cases where the conditions of the methoxylation might affect the carboxylic group, a protection step with an agent such as thionyl chloride to convert the carboxylic acid into an acid chloride followed by treatment with an alcohol under acid-catalyzed conditions (Fischer esterification) can be used.

4. **Deprotection**: If the carboxylic group was protected, the final step would involve hydrolysis of the ester group back to the carboxylic acid. Conditions such as aqueous NaOH or HCl can be employed, depending on the type of protecting group used. The product would be purified by crystallization or other suitable purification methods.

The reagents and conditions for each step must be optimized to ensure selectivity for the methoxylation at positions 2 and 6 and to maintain the integrity of the carboxylic group during the reaction. The entire synthesis should be planned considering the reactivity of the molecules involved and the desired orthogonality of protection/deprotection steps, if applicable.

Literature

• Antitubercular activities of novel benzothiazolo naphthyridone carboxylic acid derivatives endowed with high activity toward multi-drug resistant tuberculosis.

  Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20090101

• trans-Diaqua-bis(ethyl-enediamine-κN,N')copper(II) bis[3-(3-pyrid-yl)propionate] dihydrate.

  Acta crystallographica. Section E, Structure reports online 20080401

• Microsphere-based protease assays and screening application for lethal factor and factor Xa.

  Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501