Dehydro Olmesartan

Base Information

• Chemical Name: Dehydro Olmesartan
• CAS No.: 172875-98-8
• Molecular Formula: C₂₄H₂₄N₆O₂
• Molecular Weight: 428.494
• DSSTox Substance ID: DTXSID00432428
• Nikkaji Number: J715.873D
• Wikidata: Q82246489
• ChEMBL ID: CHEMBL114752
• Mol file: 172875-98-8.mol

Synonyms:Dehydro Olmesartan;172875-98-8;CHEMBL114752;5-prop-1-en-2-yl-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylic acid;starbld0000927;SCHEMBL16239998;DTXSID00432428;LLECTTOFSXVBBY-UHFFFAOYSA-N;BDBM50049113;AKOS040754864;MS-27588;HY-131277;CS-0131986;FT-0665643;1-[[2'-(1H-Tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl]-2-propyl-4-(1-methylethenyl)-1H-imidazole-5-carboxylic acid;4-Isopropenyl-2-propyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylic acid;5-Isopropenyl-2-propyl-3-[2''-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid

Chemical Property of Dehydro Olmesartan

Chemical Property:

• Melting Point: >300°C (dec.)
• Boiling Point: 704.8±70.0 °C(Predicted)
• PKA: 2.23±0.50(Predicted)
• PSA: 109.58000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 4.46230
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 428.19607403
• Heavy Atom Count: 32
• Complexity: 652

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Dehydro Olmesartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)C(=O)O)C(=C)C
• Uses: Olmesartan acid (O550001) derivative. A nonpeptide angiotensin II receptor antagonist.

Technology Process of Dehydro Olmesartan

There total 9 articles about Dehydro Olmesartan 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: 85.0%

5-Isopropenyl-2-propyl-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid ethyl ester (172875-87-5) → 1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(prop-1-en-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid (172875-98-8)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; for 5h; Ambient temperature;

DOI:10.1021/jm950450f

Reference yield:

(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl1-((2'-(1H-tetrazol-5-yl) biphenyl-4-yl)methyl)-4-(prop-1-en-2-yl)-2-propyl-1H-imidazole-5-carboxylate (879562-26-2) → 1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(prop-1-en-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid (172875-98-8)

Guidance literature:

With lithium hydroxide monohydrate; triethylamine; In 1,4-dioxane; water; at 20 ℃; for 1h;

Reference yield:

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → 1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(prop-1-en-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid (172875-98-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / HCl / Ambient temperature

2: 95 percent / diethyl ether; CH₂Cl₂ / 1 h / 10 - 15 °C

3: 1.) POCl₃, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h

4: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h

5: 94 percent / 25percent aq. AcOH / 2.5 h / 80 °C

6: 85 percent / LiOH*H₂O / dioxane; H₂O / 5 h / Ambient temperature

With pyridine; hydrogenchloride; lithium hydroxide; potassium tert-butylate; acetic acid; trichlorophosphate; In 1,4-dioxane; diethyl ether; dichloromethane; water;

DOI:10.1021/jm950450f

upstream raw materials:

5-Isopropenyl-2-propyl-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid ethyl ester

2-propyl-1H-imidazole-4,5-dicarboxylic acid

ethyl 4-isopropenyl-2-propylimidazole-5-carboxylate

diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate

Downstream raw materials:

(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl 4-isopropenyl-2-propyl-1-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate

Refernces

• 1、 Yanagisawa, Hiroaki,Amemiya, Yoshiya,Kanazaki, Takuro,Shimoji, Yasuo,Fujimoto, Koichi,Kitahara, Yoshiko,Sada, Toshio,Mizuno, Makoto,Ikeda, Masahiro,Miyamoto, Shuichi,Furukawa, Youji,Koike, Hiroyuki. "Nonpeptide angiotensin II receptor antagonists: Synthesis, biological activities, and structure - Activity relationships of imidazole-5-carboxylic acids bearing alkyl, alkenyl, and hydroxyalkyl substituents at the 4-position and their related compounds". . p. 323 - 338. Retrieved 2007/10/03.