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863031-21-4

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Basic Information

Molecular Structure:
CAS No.:	863031-21-4
Name:	1-[[2'-(2,5-Dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester
Article Data:	18
Cas Database

Formula:	C30H24N4O8
Molecular Weight:	568.543
Synonyms:	(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid;Azilsartan (medoxomil);Azilsartan Medoxomil;Azilsartan kamedoxomil;(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate;TAK 491;Azilsartan;[14C]-Azilsartan medoxomil;(5-methyl-2-oxo-1,3-dioxol-4-yl)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;UNII-LL0G25K7I2;azilsartanum medoxomilum;Edarbi;
EINECS:	1308068-626-2
Density:	1.45
PSA:	155.59000
LogP:	4.70520

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Synthetic route

: 64269-79-0
Carbonyldiimidazole

: 1449029-77-9
(5-methyl-2-oxo-2H-1,3-dioxol-4yl)methyl 2-ethoxy-1-[(4-(2-[N-hydroxy-carbamimidoyl]phenyl)phenyl)-methyl]-1H-1,3-benzodiazole-7-carboxylate

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
In dimethyl sulfoxide at 50℃; for 2h;	98.2%

: 91526-18-0
4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one

: 147403-03-0
azilsartan

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
Stage #1: 4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one; azilsartan With dmap; potassium carbonate; p-toluenesulfonyl chloride In N,N-dimethyl acetamide at 10℃; for 3h; Stage #2: In N,N-dimethyl acetamide pH=5; Stage #3: In water; acetone at 35℃; for 2h;	95%
Stage #1: 4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one; azilsartan With dmap; p-toluoylsulfonylchloride; potassium carbonate In ISOPROPYLAMIDE at -15 - 25℃; Stage #2: With hydrogenchloride In ISOPROPYLAMIDE; water for 0.5h; pH=4 - 5;	81%
With dmap; potassium carbonate; p-toluenesulfonyl chloride In N,N-dimethyl acetamide at 8 - 10℃; for 3h;	80.1%

: 1449029-80-4
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-1-{[2'-(N'-{[(4-nitrophenoxy)carbonyl]oxy}carbamimidoyl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
at 20 - 60℃; for 12h; Solvent; Temperature;	87%
With 2-methylpropyl acetate at 20 - 60℃; for 12h; Reagent/catalyst; Temperature;	87%

: 1449029-77-9
(5-methyl-2-oxo-2H-1,3-dioxol-4yl)methyl 2-ethoxy-1-[(4-(2-[N-hydroxy-carbamimidoyl]phenyl)phenyl)-methyl]-1H-1,3-benzodiazole-7-carboxylate

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
With di(succinimido) carbonate In ethyl acetate at 25 - 45℃; for 16h; Solvent; Reagent/catalyst; Temperature; Large scale;	82%
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1.5 h / 0 - 30 °C 2: 10 h / 20 - 115 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / dichloromethane; water / 1 h / 20 - 30 °C 2: 12 h / 20 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 - 30 °C 2: 2-methylpropyl acetate / 12 h / 20 - 60 °C View Scheme

: 1417575-99-5
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester of 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid dimethylacetamide

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
In water; acetone Reflux;	78%

: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-2-ethoxy-1H-benzo[d]imidazol-7-carboxylate

: 3-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
Stage #1: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-2-ethoxy-1H-benzo[d]imidazol-7-carboxylate In ethanol at 20℃; for 0.166667h; Stage #2: 3-(4'-(bromomethyl)-[1,1'-biphenyl]-2-yl)-1,2,4-oxadiazol-5(4H)-one With tetrabutylammomium bromide; potassium carbonate In ethanol at 40 - 50℃; for 10h; Reagent/catalyst; Temperature;	77.9%
With potassium carbonate; potassium iodide In dichloromethane Reflux;	72%

: 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid dicyclohexylamine salt

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
Stage #1: 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid dicyclohexylamine salt at 23 - 28℃; for 0.5h; Stage #2: With 4-chloromethyl-5-methyl-1,3-dioxol-2-one; potassium iodide at 50℃; for 3h;	76%

: 1-[{2’-(2,5-dihydro-5-oxo-1,2,4-oxodiazol-3-yl)(1,1’-biphenyl)-4-yl}methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl) methyl ester potassium salt

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
In water at 50 - 55℃; for 2h;	55%

: disodium 2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate

: 80841-78-7
4-chloromethyl-5-methyl-1,3-dioxol-2-one

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
Stage #1: disodium 2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate; 4-chloromethyl-5-methyl-1,3-dioxol-2-one In N,N-dimethyl-formamide at 20℃; for 12h; Stage #2: With hydrogenchloride In chloroform; water	14%

: C32H21Cl3N4O6

: 91526-18-0
4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one

: 863031-21-4
Azilsartan medoxomil

Conditions	Yield
With dmap In dichloromethane at 20℃; for 4h;

Raw Materials

Downstream Products

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Azilsartan medoxomil

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