Linzagolix

Base Information

• Chemical Name: Linzagolix
• CAS No.: 935283-04-8
• Molecular Formula: C₂₂H₁₅F₃N₂O₇S
• Molecular Weight: 508.432
• UNII: 7CDW97HUEX
• ChEMBL ID: CHEMBL3668014
• DSSTox Substance ID: DTXSID801337395
• NCI Thesaurus Code: C148479
• Nikkaji Number: J3.064.334H
• Pharos Ligand ID: VZSQCWK6GYLM
• RXCUI: 2621019
• Wikipedia: Linzagolix
• Mol file: 935283-04-8.mol

Synonyms:3-(5-((2,3-difluoro-6-methoxyphenyl)methoxy)-2-fluoro-4-methoxyphenyl)-2,4-dioxo-1H-thieno(3,4-d)pyrimidine-5-carboxylic acid;KLH-2109;KLH2109;linzagolix;OBE-2109;OBE2109

Chemical Property of Linzagolix

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 508.05520648
• Heavy Atom Count: 35
• Complexity: 826

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C(=C(C=C1)F)F)COC2=C(C=C(C(=C2)N3C(=O)C4=C(SC=C4NC3=O)C(=O)O)F)OC
• Recent ClinicalTrials: Extension to Study on Efficacy and Safety of Linzagolix for the Treatment of Endometriosis-associated Pain (EDELWEISS 6)
• Recent EU Clinical Trials: A long-term follow-up study to assess bone mineral density in subjects with uterine fibroids completing the Phase 3 studies of linzagolix, PRIMROSE 1 or PRIMROSE 2

Technology Process of Linzagolix

There total 9 articles about Linzagolix 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:

methyl 3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4-d]pyrimidine-5-carboxylate → 3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4- d]pyrimidine-5-carboxylic acid (935283-04-8)

Guidance literature:

methyl 3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4-d]pyrimidine-5-carboxylate; With methanol; lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 0.5h;

With hydrogenchloride; water; In tetrahydrofuran; methanol;

Reference yield:

dimethyl 4-{3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]ureido}thiophene-2,3-dicarboxylate → 3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4- d]pyrimidine-5-carboxylic acid (935283-04-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 11 - 13 ℃; for 1.5h;

Reference yield:

3-(chloromethyl)-1,2-difluoro-4-methoxybenzene (1073435-67-2) → 3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4- d]pyrimidine-5-carboxylic acid (935283-04-8)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide; tetrabutylammomium bromide / toluene; water / 4 h / 60 - 63 °C

2: acetic acid; nitric acid / 2 h / 59 - 62 °C

3: hydrogen / ethyl acetate / 4 h / 20 °C

4: triethylamine / tetrahydrofuran / 24 h / 20 °C

5: lithium hydroxide / tetrahydrofuran; methanol; water / 1.5 h / 11 - 13 °C

With tetrabutylammomium bromide; hydrogen; nitric acid; acetic acid; triethylamine; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; water; ethyl acetate; toluene;

upstream raw materials:

2,3-difluoro-6-methoxybenzaldehyde

2,3-difluoro-6-methoxybenzyl alcohol

3-(chloromethyl)-1,2-difluoro-4-methoxybenzene

1,2-difluoro-3-[(4-fluoro-2-methoxyphenoxy)methyl]-4-methoxybenzene

Downstream raw materials:

3-[2-fluoro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4- d]pyrimidine-5-carboxylic acid (2-hydroxyethyl)trimethylammonium