Velneperit

Base Information

• Chemical Name: Velneperit
• CAS No.: 342577-38-2
• Molecular Formula: C17H24 F3 N3 O3 S
• Molecular Weight: 407.457
• Mol file: 342577-38-2.mol

Synonyms:N-[5-(Trifluoromethyl)pyridin-2-yl]-trans-4-(tert-butylsulfonylamino)cyclohexane-1-carboxamide;S 2367; Velneperit

Chemical Property of Velneperit

Chemical Property:

• PKA: 11.05±0.40(Predicted)
• PSA: 96.54000
• Density: 1.31
• LogP: 4.86030
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Velneprit ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Velneperit (S-2367) is a novel Neuropeptide Y (NPY) Y5 receptor antagonist developed as a potential antiobesity drug. Its optimized synthesis involves a streamlined four-step process with improved yield (83%) and reduced environmental and safety concerns, utilizing trans-1-ethoxycarbonyl-4-aminocyclohexane hydrochloride as a starting material. Purification methods, including slurry washing and impurity-controlled recrystallization, ensure high-quality production with a 94.7% yield.

Technology Process of Velneperit

There total 9 articles about Velneperit 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:

C11H20ClNO3S (1195758-84-9) + 2-amino-5-trifluoromethylpyridine (74784-70-6) → Velneperit (342577-38-2)

Guidance literature:

With pyridine; In toluene; at 30 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.oprd.5b00023

Reference yield:

cis-4-amino-cyclohexanecarboxylic acid,methyl ester hydrochloride → Velneperit (342577-38-2)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / N,N-dimethyl-formamide / Inert atmosphere

2: ammonium molybdate tetrahydrate; dihydrogen peroxide / water / Inert atmosphere

3: sodium methylate / toluene; methanol / Inert atmosphere

4: water / Inert atmosphere

5: N,N-dimethyl-formamide; thionyl chloride / toluene / 50 °C / Inert atmosphere; Large scale

6: pyridine / toluene / 1 h / 30 °C / Inert atmosphere

With pyridine; thionyl chloride; ammonium molybdate tetrahydrate; water; dihydrogen peroxide; sodium methylate; triethylamine; N,N-dimethyl-formamide; In methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.oprd.5b00023

Reference yield:

C12H23NO3S → Velneperit (342577-38-2)

Guidance literature:

Multi-step reaction with 5 steps

1: ammonium molybdate tetrahydrate; dihydrogen peroxide / water / Inert atmosphere

2: sodium methylate / toluene; methanol / Inert atmosphere

3: water / Inert atmosphere

4: N,N-dimethyl-formamide; thionyl chloride / toluene / 50 °C / Inert atmosphere; Large scale

5: pyridine / toluene / 1 h / 30 °C / Inert atmosphere

With pyridine; thionyl chloride; ammonium molybdate tetrahydrate; water; dihydrogen peroxide; sodium methylate; N,N-dimethyl-formamide; In methanol; water; toluene;

DOI:10.1021/acs.oprd.5b00023

upstream raw materials:

C₁₁H₂₁NO₄S

C₁₁H₂₀ClNO₃S

2-amino-5-trifluoromethylpyridine

4-aminocyclohexanecarboxylic acid

Refernces

Development of an optimized synthetic and purification process of S-2367 (Velneperit), a novel neuropeptide y (NPY) Y5 receptor antagonist

10.1021/acs.oprd.5b00023

The research focuses on developing an optimized synthetic and purification process for S-2367 (Velneperit), a novel Neuropeptide Y (NPY) Y5 receptor antagonist with potential as an antiobesity drug. The purpose is to simplify the synthetic route, increase yield and productivity, and enhance environmental, health, and safety (EHS) aspects for commercial supply and clinical studies. Key chemicals used include trans-1-ethoxycarbonyl-4-aminocyclohexane hydrochloride salt (12) as the starting material, thionyl chloride (SOCl2), pyridylamine (11), and sodium bicarbonate (NaHCO3) for purification. The study concludes that by changing the starting material and reaction order, and optimizing the oxidation step with Na2WO4/H2O2 in weakly basic conditions, the overall yield increased from 59% to 83%, and the number of chemical reactions was reduced from 6 to 4. Two purification processes were developed to address a quality deviation: slurry washing with polymorphic control and salt formation of impurity 10 followed by a rational recrystallization procedure, which reliably controlled impurity levels without increasing the maximum volume, achieving a 94.7% yield of purified S-2367.

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