GDC-0810(ARN-810)

Base Information

• Chemical Name: GDC-0810(ARN-810)
• CAS No.: 1365888-06-7
• Molecular Formula: C₂₆H₂₀ClFN₂O₂
• Molecular Weight: 446.908
• Mol file: 1365888-06-7.mol

Synonyms:(E)-3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylic acid

Chemical Property of GDC-0810(ARN-810)

Chemical Property:

• Boiling Point: 622.8±55.0 °C(Predicted)
• PKA: 13.94±0.40(Predicted)
• Density: 1.342±0.06 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

Brilanestrant ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Brilanestrant is an orally bioavailable Selective Estrogen Receptor Degrader (SERD) that demonstrates robust activity in tamoxifen-resistant breast cancer xenografts. GDC-0810 functions by binding to the estrogen receptor, inducing a conformational change resulting in the degradation of the receptor. GDC-0810 or ARN-810 demonstrates robust activity in models of tamoxifen-sensitive and tamoxifen-resistant breast cancer, and is currently in clinical trials in women with locally advanced or metastatic estrogen receptor-positive breast cancer.

Technology Process of GDC-0810(ARN-810)

There total 29 articles about GDC-0810(ARN-810) 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: 97.0%

pyrrolidin-1-ium (E)-3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate → (E)-3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylic acid (1365888-06-7)

Guidance literature:

With hydrogenchloride; In water; at 30 - 40 ℃; for 0.0833333h;

Reference yield: 74.0%

1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (1082525-64-1) + (E)-tert-butyl 3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(tosyloxy)but-1-en-1-yl)phenyl)acrylate → (E)-3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylic acid (1365888-06-7)

Guidance literature:

1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole; (E)-tert-butyl 3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(tosyloxy)but-1-en-1-yl)phenyl)acrylate; With dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II); sodium hydroxide; In water; toluene; at 88 - 90 ℃; for 5h; Inert atmosphere;

With formic acid; sulfuric acid; In toluene; at 15 - 25 ℃; for 4h;

Reference yield: 52.0%

(E)-tert-butyl 3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate → (E)-3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylic acid (1365888-06-7)

Guidance literature:

With formic acid; sulfuric acid; In toluene; at 15 - 25 ℃; for 4h;

upstream raw materials:

5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

5-ethynyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

1-(tetrahydro-2H-pyran-2-yl)-5-((trimethylsilyl)ethynyl)-1H-indazole

5-(but-1-yn-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF (E)-3-(4-((E)-2-(2-CHLORO-4-FLUOROPHENYL)-1-(1H-INDAZOL-5-YL)BUT-1-EN-1-YL)PHENYL)ACRYLIC ACID". . . Retrieved 2017/05/07.
• 2、 -. "ESTROGEN RECEPTOR MODULATORS AND USES THEREOF". . . Retrieved 2012/04/04.