5-Butyl-1H-pyrazole-3-carboxylic acid

Base Information

• Chemical Name: 5-Butyl-1H-pyrazole-3-carboxylic acid
• CAS No.: 92933-48-7
• Molecular Formula: C₈H₁₂N₂O₂
• Molecular Weight: 168.195
• DSSTox Substance ID: DTXSID501288719
• Wikidata: Q27073972
• Pharos Ligand ID: S6KZPXCN5GJC
• ChEMBL ID: CHEMBL428730
• Mol file: 92933-48-7.mol

Synonyms:LUF6283

Chemical Property of 5-Butyl-1H-pyrazole-3-carboxylic acid

Chemical Property:

• PSA: 65.98000
• LogP: 1.45050
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL (clear solution; warmed)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 168.089877630
• Heavy Atom Count: 12
• Complexity: 161

Purity/Quality:

97% ^*data from raw suppliers

LUF 6283 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC1=CC(=NN1)C(=O)O
• Description: LUF6283 is a partial agonist of GPR109A/HCA2 G protein-coupled receptors (Ki = 0.55 μM in a radioligand binding assay). It stimulates [35S]-GTPγS binding and increases phosphorylation of ERK in HEK293T cells expressing GPR109A/HCA2 receptors (EC50s = 3.1 and 0.32 μM, respectively). In vivo, LUF6283 (400 mg/kg per day) reduces plasma levels of VLDL and hepatic expression of apolipoprotein B in mice.
• Uses: LUF 6283 is a partial agonist of HCA2 and is a promising drug candidate to achieve a beneficial lipid lowering effect of niacin, ultimately treating dyslipidemic disorders.

Technology Process of 5-Butyl-1H-pyrazole-3-carboxylic acid

There total 7 articles about 5-Butyl-1H-pyrazole-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.2%

5-butyl-1H-pyrazole-3-carboxylic acid ethyl ester (72894-00-9) → 5-butyl-1H-pyrazole-3-carboxylic acid (92933-48-7,890624-89-2)

Guidance literature:

With sodium hydroxide; for 5h; Heating;

DOI:10.1248/cpb.32.1568

Reference yield:

n-hexan-2-one (591-78-6) → 5-butyl-1H-pyrazole-3-carboxylic acid (92933-48-7,890624-89-2)

Guidance literature:

Multi-step reaction with 3 steps

1: EtONa / ethanol / 18 h / 20 °C

2: N₂H₄*H₂O; AcOH / 8 h / Heating

3: 20 percent / aq. NaOH / dioxane / 18 h / 20 °C

With sodium hydroxide; sodium ethanolate; hydrazine hydrate; acetic acid; In 1,4-dioxane; ethanol; 1: Claisen condensation;

DOI:10.1021/jm030888c

Reference yield:

2,4-dioxooctanoic acid ethyl ester → 5-butyl-1H-pyrazole-3-carboxylic acid (92933-48-7,890624-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N₂H₄*H₂O; AcOH / 8 h / Heating

2: 20 percent / aq. NaOH / dioxane / 18 h / 20 °C

With sodium hydroxide; hydrazine hydrate; acetic acid; In 1,4-dioxane;

DOI:10.1021/jm030888c

upstream raw materials:

2,4-dioxo-octanoic acid

5-butyl-1H-pyrazole-3-carboxylic acid ethyl ester

n-hexan-2-one

ethyl 2,4-dioxooctanoate