Piclamilast

Base Information

• Chemical Name: Piclamilast
• CAS No.: 144035-83-6
• Molecular Formula: C18H18Cl2N2O3
• Molecular Weight: 381.259
• European Community (EC) Number: 802-857-3
• UNII: WM58D7C3ZT
• DSSTox Substance ID: DTXSID3040227
• Nikkaji Number: J623.884J
• Wikipedia: Piclamilast
• Wikidata: Q7190965
• NCI Thesaurus Code: C96718
• Pharos Ligand ID: 9AKPFQRAM6ST
• Metabolomics Workbench ID: 146420
• ChEMBL ID: CHEMBL42126
• Mol file: 144035-83-6.mol

Synonyms:3-(cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide;3-cyclopentyloxy-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide;piclamilast;RP 73-401;RP 73401;RP-73-401;RP-73401

Chemical Property of Piclamilast

Chemical Property:

• Vapor Pressure: 3.26E-08mmHg at 25°C
• Refractive Index: 1.626
• Boiling Point: 447.823 °C at 760 mmHg
• PKA: 10.10±0.70(Predicted)
• Flash Point: 224.636 °C
• PSA: 63.68000
• Density: 1.37 g/cm³
• LogP: 4.39260
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 380.0694478
• Heavy Atom Count: 25
• Complexity: 438

Purity/Quality:

99%, ^*data from raw suppliers

Piclamilast ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(=O)NC2=C(C=NC=C2Cl)Cl)OC3CCCC3
• Uses: Piclamilast is a potent and selective phosphodiesterase-4 (PDE4) inhibitor. Piclamilast may offer therapeutic strategies in respiratory diseases, including asthma and chronic obstructive pulmonary disease. Piclamilast may also provide a treatment option for pre-term infants with bronchopulmonary dysplasia (BPD).

Technology Process of Piclamilast

There total 8 articles about Piclamilast 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: 84.0%

3,5-dichloro-4-aminopyridine (22889-78-7) + 3-cyclopentyloxy-4-methoxy benzoic acid chloride (144036-19-1) → piclamilast (144035-83-6)

Guidance literature:

3,5-dichloro-4-aminopyridine; With potassium tert-butylate; In toluene; at 90 ℃; Green chemistry;

3-cyclopentyloxy-4-methoxy benzoic acid chloride; In toluene; for 1h; Reagent/catalyst; Temperature; Solvent; Reflux; Green chemistry;

Reference yield: 49.9%

3,4,5-trichloropyridine (33216-52-3) + 3-(cyclopentyloxy)-4-methoxybenzamide (158429-58-4) → piclamilast (144035-83-6)

Guidance literature:

With potassium tert-butylate; In toluene; for 11h; Reflux;

Reference yield:

3-cyclopentyloxy-4-methoxybenzylaldehyde (67387-76-2) → piclamilast (144035-83-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / sulfamic acid, aq. AcOH, aq. NaClO₂ / 1 h / Ambient temperature

2: 98 percent / SOCl₂ / toluene; dimethylformamide / 5 h / Heating

3: 1.) NaH / 1.) THF, 0.25 h, 2.) THF, RT, 0.5 h

With sodium chlorite; thionyl chloride; aminosulfonic acid; sodium hydride; acetic acid; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00037a021

upstream raw materials:

3,5-dichloro-4-aminopyridine

3-cyclopentyloxy-4-methoxy benzoic acid chloride

isovanillin

Cyclopentyl bromide

Downstream raw materials:

N-(3,5-dichloro-pyridin-4-yl)-4-methoxy-3-(tetrahydro-furan-3-yloxy)benzamide

N-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxy(thiobenzamide)

N-Benzyl-N'-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxybenzamidine

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