Telcagepant

Base Information

• Chemical Name: Telcagepant
• CAS No.: 781649-09-0
• Molecular Formula: C26H27F5N6O3
• Molecular Weight: 566.531
• UNII: D42O649ALL
• ChEMBL ID: CHEMBL236593
• DSSTox Substance ID: DTXSID50999410
• Metabolomics Workbench ID: 153255
• NCI Thesaurus Code: C152545
• Nikkaji Number: J2.560.390G
• Pharos Ligand ID: T5PDUJ9B4RVY
• Wikidata: Q5675567
• Wikipedia: Telcagepant
• Mol file: 781649-09-0.mol

Synonyms:MK 0974;MK-0974;MK0974;N-((3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)hexahydro-1h-azepin-3- yl)-4-(2-oxo-2,3-dihydro-1H-imidazo(4,5-b)pyridin-1-yl)piperidine-1-carboxamide;N-(6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl)-4-(2-oxo-2,3-dihydro-1H-imidazo(4,5-b)pyridin-1-yl)piperidine-1-carboxamide;telcagepant

Chemical Property of Telcagepant

Chemical Property:

• PKA: 12.03±0.20(Predicted)
• PSA: 103.33000
• Density: 1.48 g/cm³
• LogP: 3.95310
• Solubility.: Soluble in DMSO
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 566.20647955
• Heavy Atom Count: 40
• Complexity: 948

Purity/Quality:

97% ^*data from raw suppliers

MK-0974 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(=O)N(CC1C2=C(C(=CC=C2)F)F)CC(F)(F)F)NC(=O)N3CCC(CC3)N4C5=C(NC4=O)N=CC=C5
• Isomeric SMILES: C1C[C@H](C(=O)N(C[C@@H]1C2=C(C(=CC=C2)F)F)CC(F)(F)F)NC(=O)N3CCC(CC3)N4C5=C(NC4=O)N=CC=C5
• Recent ClinicalTrials: Positron Emission Tomography (PET) Study of Brain Calcitonin Gene-Related Peptide (CGRP) Receptor Occupancy After Telcagepant Administration (MK-0974-067)
• Recent EU Clinical Trials: A Six Month Phase II/III, Randomized, Double-Blind, Placebo-Controlled Clinical Trial to Evaluate the Safety, Tolerability, and Efficacy of Telcagepant (MK-0974) for Prevention of Menstrually Related Migraine in Female Patients with Episodic Migraine

Technology Process of Telcagepant

There total 9 articles about Telcagepant 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: 93.5%

2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride + C15H16F5NO*ClH + 1,1'-carbonyldiimidazole (530-62-1) → telcagepant (781649-09-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; tert-butyl methyl ether; at 20 - 60 ℃; for 5h; Product distribution / selectivity;

Reference yield: 86.0%

2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride + (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one (781650-41-7) + 4-Nitrophenyl chloroformate (7693-46-1) → telcagepant (781649-09-0)

Guidance literature:

(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one; 4-Nitrophenyl chloroformate; With triethylamine; In tetrahydrofuran; at 0 ℃;

2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride; With triethylamine; In tetrahydrofuran; chloroform; at 25 ℃;

DOI:10.1021/ol8011524

Reference yield:

2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride + (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one (781650-41-7) → telcagepant (781649-09-0)

Guidance literature:

(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one; 4-Nitrophenyl chloroformate; With triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride; With triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 48h;

upstream raw materials:

C₁₈H₁₇F₅N₄O₂

(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one

4-Nitrophenyl chloroformate

1,1'-carbonyldiimidazole