Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate

Base Information

• Chemical Name: Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate
• CAS No.: 136285-69-3
• Molecular Formula: C23H21N3O2
• Molecular Weight: 371.43174
• Hs Code.: 2926909090
• UNII: A53V2J3N5T
• DSSTox Substance ID: DTXSID20576393
• Wikidata: Q72472313
• Mol file: 136285-69-3.mol

Synonyms:136285-69-3;Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate;ethyl 3-amino-2-[[4-(2-cyanophenyl)phenyl]methylamino]benzoate;ETHYL-3-AMINO-2-[(2'-CYANOIPHENYL-4-YL) METHYL]-AMINO BENZOATE;Azilsartan Impurity E;3-Amino-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]benzoic Acid Ethyl Ester;ETHYL 3-AMINO-2-[(2'-CYANOBIPHENYL-4-YL)METHYL]AMINOBENZOATE;ethyl 3-amino-2-[(2'-cyanobiphenyl-4-yl)methyl)aminobenzoate;Ethyl 3-amino-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]benzoate;Ethyl 3-amino-2-{[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino}benzoate;859843-08-6;A53V2J3N5T;SCHEMBL3982628;DTXSID20576393;QXQJYCWDJBDKKR-UHFFFAOYSA-N;BCP13067;AKOS015964189;DS-7046;AC-30428;CS-0328867;O11769;5-HEPTYL-2-(4-HEXYLOXYPHENYL)PYRIMIDINE;A901454;ethyl 3-amino-2-[(2'-cyanobiphenyl-4-yl)-methyl]aminobenzoate;Ethyl 3-amino-2-[(2'-cyanobiphenyl-4yl) methyl]aminobenzoate;ethyl 3-amino-2[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate;ethyl-3-amino-2-[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate;Ethyl-3-amino-2-[(2'-cyanoiphenyl-4-yl)methyl]-amino benzoate;ethyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)-methyl]amino]benzoate;ethyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate;Ethyl3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate;Benzoic acid, 3-amino-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-, ethyl ester

Chemical Property of Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate

Chemical Property:

• Boiling Point: 587.819 °C at 760 mmHg
• PKA: 4.58±0.11(Predicted)
• Flash Point: 309.302 °C
• PSA: 88.14000
• Density: 1.248 g/cm³
• LogP: 5.25048
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 371.16337692
• Heavy Atom Count: 28
• Complexity: 549

Purity/Quality:

99% ^*data from raw suppliers

3-Amino-2-[[(2''-cyano[1,1''-biphenyl]-4-yl)methyl]amino]benzoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C(=CC=C1)N)NCC2=CC=C(C=C2)C3=CC=CC=C3C#N
• Uses: 3-Amino-2-[[(2''-cyano[1,1''-biphenyl]-4-yl)methyl]amino]benzoic Acid Ethyl Esteris an impurity of Azilsartan (A926900), an analgesic and antiinflammatory drugs containing angiotensin II antagonists.

Technology Process of Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate

There total 13 articles about Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate 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: 78.0%

sodium ethanolate (141-52-6) + methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate (136304-78-4) → ethyl 3-amino-2-<<(2'-cyanobiphenyl-4-yl)methyl>amino>benzoate (136285-69-3)

Guidance literature:

In ethanol; for 1.5h; Heating;

DOI:10.1021/jm00067a016

Reference yield:

ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]amino-3-nitrobenzoate (136285-67-1) → ethyl 3-amino-2-<<(2'-cyanobiphenyl-4-yl)methyl>amino>benzoate (136285-69-3)

Guidance literature:

aluminum nickel; In tetrahydrofuran;

Reference yield:

methyl 2-carboxy-3-nitrobenzoate (21606-04-2) → ethyl 3-amino-2-<<(2'-cyanobiphenyl-4-yl)methyl>amino>benzoate (136285-69-3)

Guidance literature:

Multi-step reaction with 7 steps

1: SOCl₂, DMF / toluene / 0.5 h / Heating

2: NaN₃ / acetone; H₂O / 1 h

3: 1.5 h / Heating

4: 85 percent / K₂CO₃ / acetonitrile / 4 h / Heating

5: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature

6: 1.) FeCl₃*6H₂O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h

7: 78 percent / ethanol / 1.5 h / Heating

With hydrogenchloride; thionyl chloride; sodium azide; potassium carbonate; pyrographite; hydrazine hydrate; N,N-dimethyl-formamide; In ethanol; water; ethyl acetate; acetone; toluene; acetonitrile;

DOI:10.1021/jm00067a016

upstream raw materials:

sodium ethanolate

methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate

methyl 2-carboxy-3-nitrobenzoate

acid chloride of 1-methylhydrogen-3-nitrophthalate

Downstream raw materials:

ethyl 1-<(2'-cyanobiphenyl-4-yl)methyl>-2-(2-methylpropyl)-1H-benzimidazole-7-carboxylate

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

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

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

Refernces

• 1、 Kubo, Keiji,Kohara, Yasuhisa,Imamiya, Eiko,Sugiura, Yoshihiro,Inada, Yoshiyuki,et al.. "Nonpeptide Angiotensin II Receptor Antagonists. Synthesis and Biological Activity of Benzimidazolecarboxylic Acids". . p. 2182 - 2195. Retrieved 2007/10/02.