Paquinimod

Base Information

• Chemical Name: Paquinimod
• CAS No.: 248282-01-1
• Molecular Formula: C21H22N2O3
• Molecular Weight: 350.417
• Mol file: 248282-01-1.mol

Synonyms:N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide;N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide;Paquinimod [INN];UNII-HB76GLG27V;Paquinimod;N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide;N-ethyl-N-phenyl-1,2-dihydro-5-ethyl-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide;

Chemical Property of Paquinimod

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 487.259oC at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 248.486oC
• PSA: 62.54000
• Density: 1.267g/cm3
• LogP: 3.47320
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Paquinimod >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Paquinimod is a S100A9 inhibitor preventing S100A9 binding to TLR-4. Paquinimod reduces pathology in experimental collagenase-induced osteoarthritis. Paquinimod treatment of collagenase-induced OA (CIOA) resulted in significantly reduced synovial thickening (57%), osteophyte size at the medial femur (66%) and cruciate ligaments (67%) and cartilage damage at the medial tibia (47%) and femur (75%; n=7, untreated n=6). Paquinimod reduces leukocyte recruitment during sterile inflammation. Paquinimod also reduced priming of proinflammatory effector CD4(+) T cells.

Technology Process of Paquinimod

There total 7 articles about Paquinimod 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: 93.0%

1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester (1354639-60-3) + N-ethyl-N-phenylamine (103-69-5) → N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide (248282-01-1)

Guidance literature:

In n-heptane; for 2h; Product distribution / selectivity; Reflux; Molecular sieve;

Reference yield:

N-ethyl-N-phenylamine (103-69-5) + 5-ethyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid → N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide (248282-01-1)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 4.5h;

DOI:10.1021/jm031044w

Reference yield:

5-ethyl-1H-benzo[d][1,3]oxazine-2,4-dione (34934-06-0) → N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxo-quinoline-3-carboxamide (248282-01-1)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 5 h / 20 °C

2: NaH / dimethylformamide / 5 h / 85 °C

3: HCl / acetic acid / 6 h / 60 °C

4: SOCl₂; Et₃N / CH₂Cl₂ / 4.5 h / 0 - 20 °C

With hydrogenchloride; thionyl chloride; sodium hydride; triethylamine; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm031044w

upstream raw materials:

N-ethyl-N-phenylamine

5-ethyl-1H-benzo[d][1,3]oxazine-2,4-dione

6-ethyl-anthranilic acid

ethyl 5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-1-oxo-3-quinolinecarboxylate

Downstream raw materials:

N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide lithium salt

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