SB-705498

Base Information

• Chemical Name: SB-705498
• CAS No.: 501951-42-4
• Molecular Formula: C17H16BrF3N4O
• Molecular Weight: 429.23
• UNII: T74V9O0Y2W
• DSSTox Substance ID: DTXSID20198236
• Wikipedia: SB-705498
• Wikidata: Q27088737
• Pharos Ligand ID: H7R2Y4ACRG7H
• Metabolomics Workbench ID: 152968
• ChEMBL ID: CHEMBL207433
• Mol file: 501951-42-4.mol

Synonyms:N-(2-bromophenyl)-N'-((1-(5-trifluoromethyl-2-pyridyl)pyrrolidin-3-yl))urea;SB 705498;SB-705498;SB705498

Chemical Property of SB-705498

Chemical Property:

• Boiling Point: 506.9±50.0 °C(Predicted)
• PKA: 13.00±0.20(Predicted)
• PSA: 60.75000
• Density: 1.59
• LogP: 4.60570
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (>25 mg/ml)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 428.04596
• Heavy Atom Count: 26
• Complexity: 493

Purity/Quality:

99% ^*data from raw suppliers

1-(2-Bromophenyl)-3-[(3R)-1-[5-(trifluoromethyl)-2-pyridyl]pyrrolidin-3-yl]urea 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1NC(=O)NC2=CC=CC=C2Br)C3=NC=C(C=C3)C(F)(F)F
• Isomeric SMILES: C1CN(C[C@@H]1NC(=O)NC2=CC=CC=C2Br)C3=NC=C(C=C3)C(F)(F)F
• Recent ClinicalTrials: Intranasal SB-705498 in Allergic Rhinitis (AR) Patients
• Recent EU Clinical Trials: A randomized, double-blind, placebo controlled, incomplete block, 3 way cross over study in subjects with allergic rhinitis to assess the effect of intranasal repeat doses of SB-705498 when administered alone or in conjunction with intranasal fluticasone
• Description: The transient receptor potential vanilloid type 1 (TRPV1) receptor is a nonselective cation channel gated by noxious heat, protons, and capsaicin . SB-705498 is an orally bioavailable, competitive antagonist of the capsaicin-mediated activation of TRPV1 receptors (pKis = 7.6, 7.5, and 7.3 for human, rat, and guinea pig, respectively). It has been shown to induce rapid, reversible inhibition of capsaicin (IC50 = 3 nM)-, acid (pH 5.3)-, or heat (50°C; IC50 = 6 nM)-mediated activation of human TRPV1 (at -70 mV).

Technology Process of SB-705498

There total 3 articles about SB-705498 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%

(R)-1-(5-trifluoromethylpyridin-2-yl)pyrrolidin-3-ylamine (202267-15-0,202267-08-1) + 2-bromophenyl isocyanate (1592-00-3) → N-(2-bromophenyl)-N'-[((R)-1-(5-trifluoromethyl-2-pyridyl)pyrrolidin-3-yl)]urea (501951-42-4)

Guidance literature:

In diethyl ether;

DOI:10.1016/j.bmcl.2006.03.030

Reference yield:

[(R)-1-(5-trifluoromethylpyridin-2-yl)pyrrolidin-3-yl]-carbamic acid tert-butyl ester (717906-56-4) → N-(2-bromophenyl)-N'-[((R)-1-(5-trifluoromethyl-2-pyridyl)pyrrolidin-3-yl)]urea (501951-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / dioxane / 2 h / 80 °C

2: 84 percent / diethyl ether

With hydrogenchloride; In 1,4-dioxane; diethyl ether;

DOI:10.1016/j.bmcl.2006.03.030

Reference yield:

2-chloro-5-trifluoromethylpyridine (52334-81-3) → N-(2-bromophenyl)-N'-[((R)-1-(5-trifluoromethyl-2-pyridyl)pyrrolidin-3-yl)]urea (501951-42-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / K₂CO₃ / dimethylformamide / 7 h / 100 °C

2: aq. HCl / dioxane / 2 h / 80 °C

3: 84 percent / diethyl ether

With hydrogenchloride; potassium carbonate; In 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.03.030

upstream raw materials:

(R)-1-(5-trifluoromethylpyridin-2-yl)pyrrolidin-3-ylamine

2-bromophenyl isocyanate

[(R)-1-(5-trifluoromethylpyridin-2-yl)pyrrolidin-3-yl]-carbamic acid tert-butyl ester

2-chloro-5-trifluoromethylpyridine

Refernces