N-(4-chloropyridin-3-yl)-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)Methyl)piperazine-1-carboxaMide

Base Information

• Chemical Name: N-(4-chloropyridin-3-yl)-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)Methyl)piperazine-1-carboxaMide
• CAS No.: 1346528-50-4
• Molecular Formula: C₁₈H₁₇ClF₂N₄O₃
• Molecular Weight: 410.808
• Mol file: 1346528-50-4.mol

Synonyms:

Chemical Property of N-(4-chloropyridin-3-yl)-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)Methyl)piperazine-1-carboxaMide

Chemical Property:

• Boiling Point: 541.2±50.0 °C(Predicted)
• PKA: 12.91±0.20(Predicted)
• Density: 1.52±0.1 g/cm3(Predicted)
• Solubility.: ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide

Purity/Quality:

98% min ^*data from raw suppliers

JNJ-42165279 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: JNJ-42165279 is a potent, irreversible inhibitor of fatty acid amide hydrolase (FAAH; IC50s = 70 and 313 nM for human and rat forms, respectively). It displays selectivity for FAAH over a panel of other enzymes, receptors, transporters, and ion channels. JNJ-42165279 is active in vivo, blocking FAAH activity in brain and periphery of rats and raising concentrations of anandamide , oleoyl ethanolamide , and palmitoyl ethanolamide . It is also efficacious in the spinal nerve ligation model of neuropathic pain.

Technology Process of N-(4-chloropyridin-3-yl)-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)Methyl)piperazine-1-carboxaMide

There total 3 articles about N-(4-chloropyridin-3-yl)-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)Methyl)piperazine-1-carboxaMide 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-amino-4-chloropyridine (20511-15-3) + 1-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)piperazine (1093211-85-8) + phenyl chloroformate (1885-14-9) → JNJ-42165279 (1346528-50-4)

Guidance literature:

3-amino-4-chloropyridine; phenyl chloroformate; With pyridine; In toluene; at 2 - 5 ℃; for 7.5h; Inert atmosphere;

1-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)piperazine; With water; potassium carbonate; at 6 - 20 ℃; for 15h;

Reference yield: 84.0%

1-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)piperazine (1093211-85-8) + (4-chloro-pyridin-3-yl)carbamic acid phenyl ester (1257857-58-1) → JNJ-42165279 (1346528-50-4)

Guidance literature:

With potassium carbonate; In water; toluene; at 5 - 20 ℃; for 15h;

DOI:10.1021/acsmedchemlett.5b00353

Reference yield:

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde (656-42-8) → JNJ-42165279 (1346528-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogen / 20% palladium hydroxide-activated charcoal / toluene; methanol / 36 h / 20 - 70 °C / 760.05 Torr

2.1: pyridine / toluene / 7.5 h / 2 - 5 °C / Inert atmosphere

2.2: 15 h / 6 - 20 °C

With pyridine; hydrogen; 20% palladium hydroxide-activated charcoal; In methanol; toluene;

upstream raw materials:

2,2-difluoro-2H-1,3-benzodioxole-5-carbaldehyde

3-amino-4-chloropyridine

1-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)piperazine

phenyl chloroformate

Refernces

• 1、 -. "MODULATORS OF FATTY ACID AMIDE HYDROLASE". . . Retrieved 2011/11/30.