Verdinexor (KPT-335)

Base Information

• Chemical Name: Verdinexor (KPT-335)
• CAS No.: 1392136-43-4
• Molecular Formula: C18H12F6N6O
• Molecular Weight: 442.323
• Mol file: 1392136-43-4.mol

Synonyms:Z)-3-(3-(3,5-bis(trifluoroMethyl)phenyl)-1H-1,2,4-triazol-1-yl)-N'-(pyridin-;KPT-335;Verdinexor;Verdinexor(KPT-335);(2Z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1H-1,2,4-triazol-1-yl]- 2-propenoic acid-2-(2-pyridinyl)hydrazide;(2Z)-3-(3-(3,5-Bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)-N -(pyridin-2-yl)prop-2-enehydrazide Verdinexor(KPT-335)

Chemical Property of Verdinexor (KPT-335)

Chemical Property:

• PKA: 10.04±0.43(Predicted)
• PSA: 88.22000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: 4.90500
• Solubility.: ≥44.2 mg/mL in DMSO; insoluble in H2O; ≥2.31 mg/mL in EtOH with ultrasonic

Purity/Quality:

97% ^*data from raw suppliers

Verdinexor(KPT-335) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Verdinexor is a potent and selective SINE inhibitor, shown to be effective in treating influenza A virus infection in mice and ferret models.

Technology Process of Verdinexor (KPT-335)

There total 5 articles about Verdinexor (KPT-335) 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: 48.0%

pyrid-2-ylhydrazine (4930-98-7) + (Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylic acid (1388842-44-1) → (Z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-N'-pyridin-2-ylprop-2-enehydrazide (1392136-43-4)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at -40 ℃; for 0.5h;

Reference yield:

3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole (1333154-10-1) → (Z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-N'-pyridin-2-ylprop-2-enehydrazide (1392136-43-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 0.5 h

1.2: 1 h

2.1: lithium hydroxide; water / tetrahydrofuran / 4 h / 20 °C

3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane; ethyl acetate / 0.5 h / -40 °C

With 1,4-diaza-bicyclo[2.2.2]octane; water; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

3,5-bis(trifluoromethyl)benzonitrile (27126-93-8) → (Z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-N'-pyridin-2-ylprop-2-enehydrazide (1392136-43-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydrogen sulfide monohydrate / N,N-dimethyl-formamide / 0.42 h / 10 °C / Inert atmosphere; Large scale

1.2: 0.83 h / 10 °C / Large scale

2.1: hydrazine hydrate / N,N-dimethyl-formamide / 2 h / 10 °C / Inert atmosphere; Large scale

2.2: 13 h / 0 - 100 °C / Large scale

3.1: 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 0.5 h

3.2: 1 h

4.1: lithium hydroxide; water / tetrahydrofuran / 4 h / 20 °C

5.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane; ethyl acetate / 0.5 h / -40 °C

With 1,4-diaza-bicyclo[2.2.2]octane; sodium hydrogen sulfide monohydrate; water; hydrazine hydrate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole

(Z)-isopropyl 3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate

pyrid-2-ylhydrazine

(Z)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylic acid