Darusentan, (+/-)-

Base Information

• Chemical Name: Darusentan, (+/-)-
• CAS No.: 178306-46-2
• Molecular Formula: C22H22N2O6
• Molecular Weight: 410.426
• UNII: UAG0ANS9HZ
• DSSTox Substance ID: DTXSID30861444
• Nikkaji Number: J748.800I
• Wikidata: Q27290983
• Pharos Ligand ID: 7ZUKS1D567AS
• ChEMBL ID: CHEMBL25344
• Mol file: 178306-46-2.mol

Synonyms:Darusentan, (+/-)-;Darusentan, (RS)-;UAG0ANS9HZ;UNII-UAG0ANS9HZ;Darusentan (+/-)-form [MI];178306-46-2;CHEMBL25344;Benzenepropanoic acid, alpha-((4,6-dimethoxy-2-pyrimidinyl)oxy)-beta-methoxy-beta-phenyl-;2-(4,6-dimethoxypyrimidin-2-yl)oxy-3-methoxy-3,3-diphenylpropanoic acid;(+/-)-darusentan;SCHEMBL1068546;DTXSID30861444;FEJVSJIALLTFRP-UHFFFAOYSA-N;BDBM50050794;L001541;Q27290983;2(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl-propionic acid;2-(4,6-Dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl-propionic acid;2-(4,6-Dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionic Acid;2-[(4,6-Dimethoxypyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid;2-(4,6-Dimethoxy-pyrimidin-2-yloxy) -3-methoxy-3,3-diphenyl-propionic acid;BENZENEPROPANOIC ACID, .ALPHA.-((4,6-DIMETHOXY-2-PYRIMIDINYL)OXY)-.BETA.-METHOXY-.BETA.-PHENYL-

Chemical Property of Darusentan, (+/-)-

Chemical Property:

• PSA: 100.00000
• LogP: 2.91600
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 410.14778643
• Heavy Atom Count: 30
• Complexity: 506

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=NC(=N1)OC(C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)OC

Technology Process of Darusentan, (+/-)-

There total 6 articles about Darusentan, (+/-)- 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: 90.0%

(S)-methyl-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate (178306-45-1) → (.S)-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl propionic acid (178306-46-2)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; at 100 ℃; for 3h;

Reference yield:

(S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid (178306-52-0,178306-49-5) → (.S)-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl propionic acid (178306-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate; dimethyl sulfate / water; N,N-dimethyl-formamide

2: potassium carbonate / water; n-heptane; N,N-dimethyl-formamide; ethyl acetate; acetonitrile

3: water; 1,4-dioxane

With sodium methylate; potassium carbonate; dimethyl sulfate; In 1,4-dioxane; n-heptane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

3,3-diphenyloxirane-2-carboxylic acid methyl ester (76527-25-8) → (.S)-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl propionic acid (178306-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / BF₃*Et₂O / 0.33 h / 0 °C

2: 1.) K₂CO₃ / 1.) DMF, 0.5 h, 2.) DMF, 90 deg C, 3 h

3: 62 percent / 1 N aq. NaOH / dioxane / 3 h / 80 °C

With sodium hydroxide; boron trifluoride diethyl etherate; potassium carbonate; In 1,4-dioxane;

DOI:10.1021/jm960274q

upstream raw materials:

(S)-methyl-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate

benzophenone

3,3-diphenyloxirane-2-carboxylic acid methyl ester

2-hydroxy-3-methoxy-3,3-diphenylpropionicacid methyl ester

Downstream raw materials:

methyl 3,3-dicyclohexyl-2-hydroxy-3-methoxypropionate

Refernces

• 1、 -. "Process for the Preparation of an Endothelin Receptor Antagonist". Page/Page column. . Retrieved 2014/09/29.
• 2、 -. "Carboxylic acid derivatives, their preparation and use". . . Retrieved 2008/06/13.