5932-32-1 | Cyclopentapyrazole-3-carboxylic acid

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$40.00	$28.00
1g	95%	in stock	$44.00	$31.00
5g	95%	in stock	$99.00	$69.00
25g	95%	in stock	$448.00	$314.00
100g	95%	in stock	$1,317.00	$922.00

Description

• Catalog Number: AB43156
• Chemical Name: Cyclopentapyrazole-3-carboxylic acid
• CAS Number: 5932-32-1
• Molecular Formula: C7H8N2O2
• Molecular Weight: 152.1506
• MDL Number: MFCD01248822
• SMILES: OC(=O)c1n[nH]c2c1CCC2

Computed Properties

• Complexity: 183
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1
• XLogP3: 0.8

Upstream Synthesis Route

To synthesize Cyclopentapyrazole-3-carboxylic acid, one potential route could involve the following steps:

1. Cyclopentanone Synthesis: The starting material for the ring structure can be synthesized by a cyclization reaction using adipic acid or by a [4+1] cycloaddition reaction of 1,3-dienes in the presence of a suitable catalyst.

2. Diazotization Reaction: The keto group of cyclopentanone can be converted to the corresponding hydrazone by reaction with hydrazine. This is then followed by diazotization using nitrous acid, which is typically generated in situ from a nitrite salt and a strong acid.

3. Pyrazole Formation: The diazo compound can undergo intramolecular cyclization to form the pyrazole ring. This can be facilitated by the addition of a base, such as sodium ethoxide, which can assist by deprotonating the intermediate, thus promoting ring closure to form the pyrazole core.

4. Carboxylation: Introduction of the carboxylic acid function at the C-3 position of the pyrazole can be accomplished through various methods, such as the Sandmeyer reaction where a diazonium group is replaced by carboxylate using copper(I) chloride followed by hydrolysis, or by the use of diazomethane followed by oxidation of the resulting methyl group.

5. Purification: The crude Cyclopentapyrazole-3-carboxylic acid may be purified by recrystallization or column chromatography, depending on the impurities present and the scale of the synthesis.

It is important to note that the specific conditions, such as temperature, solvent, and reaction times will need to be optimized for each step, and the safety precautions must be observed, especially when handling potentially hazardous reagents such as hydrazine and nitrous acid. Moreover, further functional group manipulations may be required depending on the starting materials and specific synthetic route chosen.

Literature

• Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

  Bioorganic & medicinal chemistry letters 20101101

• Nicotinic acid receptor agonists.

  Journal of medicinal chemistry 20081225

• 3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro-cyclopentapyrazole (MK-0354): a partial agonist of the nicotinic acid receptor, G-protein coupled receptor 109a, with antilipolytic but no vasodilatory activity in mice.

  Journal of medicinal chemistry 20080828

• Agonist lead identification for the high affinity niacin receptor GPR109a.

  Bioorganic & medicinal chemistry letters 20070901

• Pyrazole derivatives as partial agonists for the nicotinic acid receptor.

  Journal of medicinal chemistry 20030828