GS9620

Base Information

• Chemical Name: GS9620
• CAS No.: 1228585-88-3
• Molecular Formula: C22H30N6O2
• Molecular Weight: 410.519
• Mol file: 1228585-88-3.mol

Synonyms:CS-1352;4-amino-2-butoxy-8-(3-(pyrrolidin-1-ylmethyl)benzyl)-7,8-dihydropteridin-6(5H)-one;UNII-O8M467C50G;4-amino-2-n-butoxy-8-[3'-(pyrrolidin-1"-ylmethyl)-benzyl]-5,6,7,8-tetrahydropteridin-6-one;GS-9620;8-(3-(pyrrolidin-1-ylmethyl)benzyl)-4-amino-2-butoxy-7,8-dihydropteridin-6(5H)-one;

Chemical Property of GS9620

Chemical Property:

• PKA: 10.34±0.20(Predicted)
• PSA: 100.10000
• Density: 1.247±0.06 g/cm3(Predicted)
• LogP: 3.46140
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (10 mg/ml)

Purity/Quality:

98% ^*data from raw suppliers

GS-9620(Vesatolimod) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: GS-9620 is a potent and selective oral Toll-like receptor 7 (TLR7) agonist that directly activates plasmacytoid dendritic cells (pDCs). GS-9620 suppressed hepatitis B virus (HBV) in animal models of chronic infection and transiently activated HIV expressionex vivoin latently-infected peripheral blood mononuclear cells (PBMCs) from virally suppressed patients. Currently, GS-9620 is under clinical evaluation for treating chronic HBV infection and for reducing latent reservoirs in virally-suppressed HIV-infected patients.

Technology Process of GS9620

There total 7 articles about GS9620 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:

ethyl 2-((6-amino-2-butoxy-5-nitropyrimidin-4-yl)(3-(pyrrolidin-1-ylmethyl)benzyl)amino)acetate hydrochloride → 4-amino-2-n-butoxy-8-[3’-(pyrrolidin-1“-ylmethyl)-benzyl]-5,6,7,8-tetrahydropteridin-6-one (1228585-88-3)

Guidance literature:

ethyl 2-((6-amino-2-butoxy-5-nitropyrimidin-4-yl)(3-(pyrrolidin-1-ylmethyl)benzyl)amino)acetate hydrochloride; With acetic acid; In water; at 20 ℃; for 0.25h;

With zinc; In water; at 20 - 40 ℃; for 0.16h;

Reference yield:

ethyl 2-((6-amino-2-butoxy-5-nitropyrimidin-4-yl)(3-(pyrrolidin-1-ylmethyl)benzyl)amino)acetate (1228588-13-3) → 4-amino-2-n-butoxy-8-[3’-(pyrrolidin-1“-ylmethyl)-benzyl]-5,6,7,8-tetrahydropteridin-6-one (1228585-88-3)

Guidance literature:

With hydrogen; In methanol; water; for 1.5h;

Reference yield:

ethyl 2-((6-amino-2-(methylthio)-5-nitropyrimidin-4-yl)(3-(pyrrolidin-1-ylmethyl)benzyl)amino)acetate (1228587-56-1) → 4-amino-2-n-butoxy-8-[3’-(pyrrolidin-1“-ylmethyl)-benzyl]-5,6,7,8-tetrahydropteridin-6-one (1228585-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tungstate (VI) dihydrate; acetic acid; dihydrogen peroxide / water; ethanol / 19 h / 0 °C

2.1: trifluoroacetic acid / 1 h / 100 °C

3.1: hydrogen / methanol / 1.5 h

3.2: pH 1-2

With sodium tungstate (VI) dihydrate; hydrogen; dihydrogen peroxide; acetic acid; trifluoroacetic acid; In methanol; ethanol; water;

upstream raw materials:

ethyl 2-((6-amino-2-butoxy-5-nitropyrimidin-4-yl)(3-(pyrrolidin-1-ylmethyl)benzyl)amino)acetate

ethyl 2-(3-(pyrrolidin-1-ylmethyl)benzylamino)acetate

(3-(pyrrolidin-1-ylmethyl)phenyl)methanamine

ethyl 2-((6-amino-2-(methylthio)-5-nitropyrimidin-4-yl)(3-(pyrrolidin-1-ylmethyl)benzyl)amino)acetate

Downstream raw materials:

4-amino-2-n-butoxy-8-[3'-(pyrrolidin-1-ylmethyl)-benzyl]-5,6,7,8-tetrahydropteridin-6-one hydrochloride

C₂₂H₃₀N₆O₃

C₂₂H₂₈N₆O₃

Refernces

• 1、 -. "METHODS FOR TREATING HCV". Page/Page column 96. . Retrieved 2013/03/28.
• 2、 -. "METHODS FOR TREATING HCV". Paragraph 0363; 0364. . Retrieved 2013/10/22.