MK 0974, Telcagepant

Base Information

• Chemical Name: MK 0974, Telcagepant
• CAS No.: 781649-09-0
• Molecular Formula: C26H27F5N6O3
• Molecular Weight: 566.531
• Mol file: 781649-09-0.mol

Synonyms:MK 0974;Telcagepant;

Chemical Property of MK 0974, Telcagepant

Chemical Property:

• PKA: 12.03±0.20(Predicted)
• PSA: 103.33000
• Density: 1.48 g/cm³
• LogP: 3.95310
• Solubility.: Soluble in DMSO

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of MK 0974, Telcagepant

There total 9 articles about MK 0974, 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

Refernces

• 1、 Burgey, Christopher S.,Paone, Daniel V.,Shaw, Anthony W.,Deng, James Z.,Nguyen, Diem N.,Potteiger, Craig M.,Graham, Samuel L.,Vacca, Joseph P.,Williams, Theresa M.. "Synthesis of the (3R,6S)-3-amino-6-(2,3-difluorophenyl)azepan-2-one of telcagepant (MK-0974), a calcitonin gene-related peptide receptor antagonist for the treatment of migraine headache". supporting information; experimental part. p. 3235 - 3238. Retrieved 2009/05/27.
• 2、 -. "PROCESS FOR THE PREPARATION OF PYRIDINE HETEROCYCLE CGRP ANTAGONIST INTERMEDIATE". Page/Page column 18; 19; 22; 23-24. . Retrieved 2008/06/13.