Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Base Information

• Chemical Name: Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
• CAS No.: 147403-65-4
• Molecular Formula: C25H24N4O4
• Molecular Weight: 444.49
• European Community (EC) Number: 692-067-3
• Mol file: 147403-65-4.mol

Synonyms:147403-65-4;Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate;1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-[[2'-[(hydroxyamino)iminomethyl][1,1'-biphenyl]-4-yl]methyl]-, methyl ester;SCHEMBL16367902;AMY4361;DTXSID10570360;MFCD21496678;AKOS016004226;DS-3760;AC-25906;Methyl 2-ethoxy-1-{[2'-(N'-hydroxycarbamimidoyl)[1,1'-biphenyl]-4-yl]methyl}-1H-benzimidazole-7-carboxylate

Chemical Property of Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Chemical Property:

• Melting Point: 207-209℃
• Boiling Point: 657.2±65.0 °C(Predicted)
• PKA: 6.77±0.69(Predicted)
• PSA: 109.46000
• Density: 1.29
• LogP: 4.73170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 444.17975526
• Heavy Atom Count: 33
• Complexity: 681

Purity/Quality:

98%MIN ^*data from raw suppliers

2-Ethoxy-1-[[2''-[(hydroxyamino)iminomethyl][1,1''-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=NO)N)C(=O)OC
• Isomeric SMILES: CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4/C(=N/O)/N)C(=O)OC
• Uses: Azilsartan (A926900) derivative. Intermediate in the synthesis of angiotensin II receptor antagonist.

Technology Process of Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

There total 7 articles about Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate 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: 96.9%

→ methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate (147403-65-4)

Guidance literature:

Product distribution / selectivity;

Reference yield: 90.0%

methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate (139481-44-0) → methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate (147403-65-4)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydrogencarbonate; In N,N-dimethyl acetamide; water; at 70 ℃; for 18h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 71.7%

methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate (139481-44-0) → methyl 1-[(2'-carbamoylbiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate (147404-76-0) + methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate (147403-65-4)

Guidance literature:

With hydroxylamine; triethylamine; In ethanol; water; for 20h; Solvent; Reagent/catalyst; Temperature; Reflux;

upstream raw materials:

methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate

methyl 2-ethoxy-1-((2'-(N'-(methoxycarbonyloxy)carbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate

Downstream raw materials:

azilsartan

2-ethoxy-1-[[2'-[N'((ethoxycarbonyl)oxy)carbamimidoyl][1,1-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid methyl ester

methyl 2-oxo-3-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate

methyl 2-ethoxy-1-((2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d]-imidazole-7-carboxylate

Refernces

• 1、 -. "High-purity, small-particle-diameter and low-solvent-residue azilsartan bulk drug and preparation method thereof". Paragraph 0091. . Retrieved 2019/01/06.
• 2、 -. "Method for simply and conveniently synthesizing azilsartan". Paragraph 0033; 0035; 0036. . Retrieved 2018/11/22.