ChemicalBook CAS DataBase List 1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, Methyl ester

1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, Methyl ester synthesis

10synthesis methods

Product Name:1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, Methyl ester
CAS Number:147403-52-9
Molecular formula:C26H22N4O5
Molecular Weight:470.48

139481-44-0 Synthesis

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

139481-44-0
329 suppliers
$9.00/5g

530-62-1 Synthesis

530-62-1
935 suppliers
$6.00/25g

1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, Methyl ester

147403-52-9
226 suppliers
$9.00/250mg

Yield:147403-52-9 96.7%

Reaction Conditions:

Stage #1:methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate with hydroxylamine hydrochloride;1,8-diazabicyclo[5.4.0]undec-7-ene in 1,4-dioxane at 80 - 95; for 0.5 h;
Stage #2:1,1'-carbonyldiimidazole in 1,4-dioxane for 1 h;Reagent/catalyst;Temperature;

Steps:

4 preparation of Azilsartan methyl ester
Hydroxylamine hydrochloride (33.4 g, 0.48 mol),DBU (109.5 g, 0.72 mol) plusTo 190ml dioxane at room temperature for 30min,JoinMethyl 2-ethoxy-1- (2'-cyanobiphenyl-4-yl) methylbenzimidazole-7-carboxylate(32.9 g, 0.08 mol),The reaction was stirred at 80-85 ° C until TLC showed complete reaction (about 11h)After cooling to room temperature N'N-carbonyldiimidazole (13.0 g, 0.08 mol)Stirring 1h,The solvent was evaporated under reduced pressure, water 160ml,Stirring 8% diluted hydrochloric acid to adjust the pH to 4,Suction filtration, washed with water, washed with dichloromethane, dried to give a white powder 36.4g, a yield of 96.7%.

References:

The Chinese People's Liberation Army The Second San○ Hospital;Shenyang Pharmaceutical University;Shandong Weigao Pharmaceutical Co., Ltd.;Yuan Zhenting;Wang Shaojie;Zhao Yong;Qu Huaping;Han Jiangsheng CN104230909, 2018, B Location in patent:Paragraph 0029; 0038; 0043; 0046-0048

FullText

147404-82-8 Synthesis