Telmisartan tert-Butyl Ester

Base Information

• Chemical Name: Telmisartan tert-Butyl Ester
• CAS No.: 144702-26-1
• Molecular Formula: C37H38N4O2
• Molecular Weight: 570.734
• UNII: H4HLP8PW27
• DSSTox Substance ID: DTXSID10162789
• Nikkaji Number: J3.655.350B
• Wikidata: Q27279635
• Mol file: 144702-26-1.mol

Synonyms:144702-26-1;Telmisartan tert-Butyl Ester;4'-[[1,4'-Dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl]-methyl]-1,1'-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester;Tacrolimus methylacryl aldehyde;Telmisartan EP Impurity C;UNII-H4HLP8PW27;H4HLP8PW27;Telmisartan specified impurity C [EP];tert-butyl 2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]methyl]phenyl]benzoate;(E)-3-((1R,3R,4R)-4-Hydroxy-3-methoxycyclohexyl)-2-methylacrylaldehyde;(1,1'-Biphenyl)-2-carboxylic acid, 4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl)methyl)-, 1,1-dimethylethyl ester;1,1-Dimethylethyl 4'-((4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl)methyl)biphenyl-2-carboxylate;Tacrolimus impurity, tacrolimus methylacryl aldehyde- [USP];Telmisartan impurity, telmisartan tert-butyl ester- [USP];2-Propenal, 3-(4-hydroxy-3-methoxycyclohexyl)-2-methyl-, (1R-(1alpha(E),3alpha,4beta))-;[1,1'-Biphenyl]-2-carboxylic acid, 4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]-, 1,1-dimethylethyl ester;4/'-[[1,4/'-Dimethyl-2/'-propyl(2,6/'-bi-1H-benzimidazol)-1/'-yl]-methyl]-1,1/'-biphenyl-2-carboxyli;1,1-dimethylethyl 4'-[[4-methyl-6-(1-methyl-1h-benzimidazol-2-yl)-2-propyl-1h-benzimidazol-1-yl]methyl]biphenyl-2-carboxylate;4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1h-benzimidazol)-1'-yl)-methyl)-1,1'-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester;SCHEMBL170874;DTXSID10162789;JSCFLEBEWCTASN-UHFFFAOYSA-N;AKOS015896036;CS-O-08260;AC-26340;FT-0657482;TELMISARTAN IMPURITY C [EP IMPURITY];J3.655.350B;A808271;J-007999;Q27279635;TACROLIMUS IMPURITY, TACROLIMUS METHYLACRYL ALDEHYDE- [USP IMPURITY];TELMISARTAN IMPURITY, TELMISARTAN TERT-BUTYL ESTER- [USP IMPURITY];1,1-Dimethylethyl 4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl][1,1'-biphenyl]-2-carboxylate;Telmisartan Imp C (EP);Telmisartan Impurity C;1,1-Dimethylethyl 4'-[[4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylate (Telmisartan tert-Butyl Ester);2-PROPENAL, 3-(4-HYDROXY-3-METHOXYCYCLOHEXYL)-2-METHYL-, (1R-(1.ALPHA.(E),3.ALPHA.,4.BETA.))-;4'-[[1,4'-DIMETHYL-2'-PROPYL(2,6'-BI-1H-BENZIMIDAZOL)-1'-YL]-METHYL]-1,1'-BIPHENYL-2-CARBOXYLICACID1,1-DIMETHYLETHYLESTER;4'-[[1,4'-Dimethyl-2'-propyl-2,6'-bi[1H-benzoimidazole]-1'-yl]methyl]-1,1'-biphenyl-2-carboxylic acid tert-butyl ester;tert-Butyl 4'-((1,7'-dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carboxylate;tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazol-1-yl]methyl]biphenyl-2-carboxylate;tert-butyl 4'-{[4-methyl-6-(1-methyl-1H-1,3-benzodiazol-2-yl)-2-propyl-1H-1,3-benzodiazol-1-yl]methyl}-[1,1'-biphenyl]-2-carboxylate;tert.-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate

Chemical Property of Telmisartan tert-Butyl Ester

Chemical Property:

• Appearance/Colour: White to off-white powder
• Boiling Point: 780.446 °C at 760 mmHg
• PKA: 5.00±0.10(Predicted)
• Flash Point: 425.798 °C
• PSA: 61.94000
• Density: 1.162 g/cm³
• LogP: 8.52150
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 570.29947647
• Heavy Atom Count: 43
• Complexity: 928

Purity/Quality:

99% ^*data from raw suppliers

Telmisartantert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1=NC2=C(N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=O)OC(C)(C)C)C=C(C=C2C)C5=NC6=CC=CC=C6N5C
• Uses: Telmisartan tert-Butyl Ester is an impurity of Telmisartan (T017000). Telmisartan impurity C. Telmisartan tert-Butyl Ester (Telmisartan EP Impurity C) is an impurity of Telmisartan (T017000). Telmisartan impurity C.

Technology Process of Telmisartan tert-Butyl Ester

There total 9 articles about Telmisartan tert-Butyl Ester 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: 86.0%

4'-bromomethyl-biphenyl-2-carboxylic acid tert-butyl ester (114772-40-6) + 2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole (152628-02-9) → tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate (144702-26-1)

Guidance literature:

With potassium tert-butylate; In 1-methyl-pyrrolidin-2-one; at 10 ℃; for 4h;

Reference yield: 64.0%

tert-butyl 4'-((6-formyl-4-methyl-2-n-propyl-1H-benzimidazol-1-yl)methyl)biphenyl-2-carboxylate (1190092-31-9) + 2-nitro-N-methylaniline (612-28-2) → tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate (144702-26-1)

Guidance literature:

tert-butyl 4'-((6-formyl-4-methyl-2-n-propyl-1H-benzimidazol-1-yl)methyl)biphenyl-2-carboxylate; 2-nitro-N-methylaniline; In ethanol; for 0.5h;

With sodium dithionite; In ethanol; water; at 50 ℃;

Reference yield:

methyl 4-amino-3-methylbenzoate (18595-14-7) → tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate (144702-26-1)

Guidance literature:

Multi-step reaction with 7 steps

1: chlorobenzene / 100 °C

2: fuming HNO₃, 60percent H₂SO₄ / 0 °C

3: H₂ / 10percent Pd/C / methanol / 50 °C / 3750.3 Torr

4: glacial CH₃COOH / 1.5 h / Heating

5: 5.46 g / aq. NaOH / methanol / 2 h / Heating

6: 5.86 g / polyphosphoric acid / 20 h / 150 °C

7: 1.) t-BuOK / 1.) DMSO, RT, 30 min, 2.) DMSO, 14 h

With sodium hydroxide; PPA; sulfuric acid; potassium tert-butylate; hydrogen; nitric acid; acetic acid; palladium on activated charcoal; In methanol; chlorobenzene;

DOI:10.1021/jm00077a007

upstream raw materials:

4'-bromomethyl-biphenyl-2-carboxylic acid tert-butyl ester

2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole

methyl 4-amino-3-methylbenzoate

N-methylbenzene-1,2-diamine dihydrochloride

Downstream raw materials:

telmisatran

Refernces

• 1、 -. "Telmisartan alkyl ester (by machine translation)". Paragraph 0049. . Retrieved 2018/10/31.
• 2、 -. "PROCESS FOR PREPARING TELMISARTAN". Page/Page column 14. . Retrieved 2011/01/12.