Tecovirimat

Base Information

• Chemical Name: Tecovirimat
• CAS No.: 816458-31-8
• Molecular Formula: C₁₉H₁₅F₃N₂O₃
• Molecular Weight: 376.335
• Mol file: 816458-31-8.mol

Synonyms:tecovirimat;rel-N-[(3aR,4R,4aR,5aS,6S,6aS)-3,3a,4,4a,5,5a,6,6a-Octahydro-1,3-dioxo-4,6-ethenocycloprop[f]isoindol-2(1H)-yl]-4-(trifluoromethyl)benzamide

Chemical Property of Tecovirimat

Chemical Property:

• Melting Point: 194-195ºC
• PSA: 66.48000
• Density: 1.53g/cm3
• LogP: 2.73210
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane (Slightly), DMSO Slightly()

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Tecovirimat is an orally bioavailable antipoxvirus compound inhibits extracellular virus formation and protects mice from lethal orthopoxvirus, including vaccinia, monkeypox, camelpox, cowpox, ectromelia (mousepox), and variola viruses.

Technology Process of Tecovirimat

There total 21 articles about Tecovirimat 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: 87.0%

(3aα,4β,4aα,5aα,6β,6aα)-4,4a,5,5a,6,6a-hexahydro-4,6-etheno-1H-cycloprop[f]isobenzofuran-1,3(3aH)-dione (944-41-2) + 4-(trifluoromethyl)benzoic acid hydrazide (339-59-3) → Tecovirimat (816458-31-8,869572-92-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; for 4.5h; Heating;

DOI:10.1021/jm061484y

Reference yield: 65.4%

N-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-4-(trifluoromethyl)benzamide (1565736-80-2) + Cyclohepta-1,3,5-triene (544-25-2) → Tecovirimat (816458-31-8,869572-92-9)

Guidance literature:

In toluene; at 95 - 110 ℃; for 26.5h; Inert atmosphere;

Reference yield: 51.0%

4-(trifluoromethyl)benzoic acid hydrazide (339-59-3) + C11H10O3 → 4-trifluoromethyl-N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop[f]isoindol-2(1H)-yl)-benzamide (816458-31-8,869572-92-9)

Guidance literature:

In ethanol; Heating; Inert atmosphere;

upstream raw materials:

(3aα,4β,4aα,5aα,6β,6aα)-4,4a,5,5a,6,6a-hexahydro-4,6-etheno-1H-cycloprop[f]isobenzofuran-1,3(3aH)-dione

4-(trifluoromethyl)benzoic acid hydrazide

Cyclohepta-1,3,5-triene

N-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-4-(trifluoromethyl)benzamide

Refernces

• 1、 -. "METHODS OF PREPARING TECOVIRIMAT". . . Retrieved 2014/03/22.
• 2、 Bailey, Thomas R.,Rippin, Susan R.,Opsitnick, Elizabeth,Burns, Christopher J.,Pevear, Daniel C.,Collett, Marc S.,Rhodes, Gerry,Tohan, Sanjeev,Huggins, John W.,Baker, Robert O.,Kern, Earl R.,Keith, Kathy A.,Dai, Dongcheng,Yang, Guang,Hruby, Dennis,Jordan, Robert. "N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethenocycloprop[f] isoindol-2-(1H)-yl)carboxamides: Identification of novel orthopoxvirus egress inhibitors". . p. 1442 - 1444. Retrieved 2007/10/03.