Olmesartan medoxomil supplier | CasNO.144689-63-4

Name
Olmesartan medoxomil
EINECS 604-433-1
CAS No. 144689-63-4
Article Data49
CAS DataBase
Density 1.38 g/cm³
Solubility
Melting Point 180 °C
Formula C₂₉H₃₀N₆O₆
Boiling Point 804.2 °C at 760 mmHg
Molecular Weight 558.594
Flash Point 440.2 °C
Transport Information
Appearance White to off-white crystalline powder
Safety
Risk Codes R36/38; R41; R38
Molecular Structure
Hazard Symbols Xi
Synonyms Olmetec (TN);Cs 866;Benicar (TN);Benicar;Olmetec;1H-Imidazole-5-carboxylic acid,4-(1-hydroxy-1-methylethyl)-2-propyl- 1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]- methyl]-,(5-methyl-2-oxo-1,3-dioxol-4-yl)- methyl ester;(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate;4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl-1H-Imidazole-5-carboxylic acid, (5-methyl -2-oxo-1,3-dioxol-4-yl;Olmesartan(144689-63-4);1H-Imidazole-5-carboxylic acid;
PSA 162.16000
LogP 4.17000

Synthetic route

: 144690-92-6
trityl olmesartan medoxomil

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
With acetic acid In water at 25℃; for 1h;	100%
With hydrogenchloride In water; toluene at 20℃; for 2.5h;	98.6%
With TRILITE SCR-10 gel type In methanol for 6h; Product distribution / selectivity; Reflux;	94%

: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-({2'-[1-(2,4-dimethoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 25℃; for 6h; Time;	98%

: 144690-92-6
trityl olmesartan medoxomil

A: 76-84-6
triphenylmethyl alcohol

B: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Stage #1: trityl olmesartan medoxomil With sulfuric acid; water In acetone at 40℃; for 2 - 4h; Stage #2: With sodium hydrogencarbonate at 20℃; for 1h;	A n/a B 90%
With water In acetone for 14h; Product distribution / selectivity; Heating / reflux;	A n/a B 73%
With water In acetonitrile for 14h; Product distribution / selectivity; Heating / reflux;	A n/a B 71%

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

: 172875-59-1
ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Stage #1: ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate With sodium hydroxide In N,N-dimethyl acetamide at 10 - 15℃; for 8h; Stage #2: 4-chloromethyl-5-methyl-1,3-dioxol-2-one With potassium carbonate In N,N-dimethyl acetamide at 0 - 65℃; for 10h;	90%

: trityl olmesartan medoxomil

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
With hydrogenchloride In water; toluene at 20℃; for 3h;	89%

: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-1-({2'-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-2-propyl-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
With trifluoroacetic acid at 25℃; for 72h; Temperature;	83%

: 1020157-01-0
(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2′-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
With acetic acid at 80℃; for 2.5h;	81%
With sulfuric acid In water; acetone at 50 - 55℃; for 2h;	80%
With acetic acid In water at 55 - 60℃; for 2 - 3h; Product distribution / selectivity;
With hydrogenchloride In methanol; dichloromethane at 0 - 5℃; for 1 - 2h;

: 144690-33-5
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
	71%
Multi-step reaction with 2 steps 1.1: diisopropylamine; sodium hydroxide / toluene; ISOPROPYLAMIDE / 4 h / 25 - 45 °C 1.2: 8 h / 40 - 70 °C 1.3: 25 - 35 °C / pH ~ 6 - 7 2.1: hydrogenchloride; water / methanol / 1 h / 0 - 35 °C 2.2: 25 - 35 °C / pH ~ 3 - 4 View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate; water / acetone / 16 h / 20 °C 2.1: potassium carbonate; potassium iodide / acetone / 3 h / 50 - 55 °C 3.1: hydrogenchloride; water / toluene / 3 h / 20 °C 3.2: 15 - 20 °C / pH 4.5 - 5.5 View Scheme

: 58954-23-7
2-propyl-1H-imidazole-4,5-dicarboxylic acid

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 86 percent / HCl / Ambient temperature 2: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 4: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature 5: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C 6: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C View Scheme

: 133051-88-4
N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature 3: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C 4: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C View Scheme
Multi-step reaction with 4 steps 1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C 2: potassium hydroxide; water / N,N-dimethyl-formamide / 22 h / 54 - 56 °C 3: potassium iodide; potassium carbonate / 20 °C 4: sulfuric acid / water; acetone / 2 h / 50 - 55 °C View Scheme

: 144689-94-1
2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 3: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature 4: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C 5: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C View Scheme

: 144689-93-0
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature 3: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C 4: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / toluene / 0.75 h / 45 - 50 °C 1.2: 10 h / 60 - 70 °C 2.1: diisopropylamine; sodium hydroxide / toluene; ISOPROPYLAMIDE / 4 h / 25 - 45 °C 2.2: 8 h / 40 - 70 °C 2.3: 25 - 35 °C / pH ~ 6 - 7 3.1: hydrogenchloride; water / methanol / 1 h / 0 - 35 °C 3.2: 25 - 35 °C / pH ~ 3 - 4 View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / tetrabutylammomium bromide / acetone / 15 h / 50 - 55 °C 2.1: potassium carbonate; water / acetone / 16 h / 20 °C 3.1: potassium carbonate; potassium iodide / acetone / 3 h / 50 - 55 °C 4.1: hydrogenchloride; water / toluene / 3 h / 20 °C 4.2: 15 - 20 °C / pH 4.5 - 5.5 View Scheme

: 172875-59-1
ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature 2: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C 3: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide; water / N,N-dimethyl-formamide / 22 h / 54 - 56 °C 2: potassium iodide; potassium carbonate / 20 °C 3: sulfuric acid / water; acetone / 2 h / 50 - 55 °C View Scheme

: 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5yl]biphenyl-4-yl]methyl]imidazole-5-carboxylic acid lithium salt

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C 2: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C View Scheme

: 51802-42-7
2-propylimidazole-4,5-dicarbonitrile

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 80 percent / 6N aq. HCl / 8 h / Heating 2: 86 percent / HCl / Ambient temperature 3: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 4: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 5: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature 6: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C 7: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 80 percent / 6N aq. HCl / 8 h / Heating
2: 86 percent / HCl / Ambient temperature
3: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C
4: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
5: LiOH*H2O / dioxane; H2O / 20 h / Ambient temperature
6: 88 percent / K2CO3 / N,N-dimethyl-acetamide / 4 h / 20 - 50 °C
7: 81 percent / 25percent aq. AcOH / 2.5 h / 80 °C
View Scheme

: olmesartan medoxomil hydrobromide

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 0 - 20℃; for 2 - 3h; pH=5.6; Product distribution / selectivity;

: 144690-92-6
trityl olmesartan medoxomil

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

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Stage #1: trityl olmesartan medoxomil With hydrogenchloride; ethanol; water at 24 - 26℃; for 3h; Stage #2: 4-chloromethyl-5-methyl-1,3-dioxol-2-one With sodium hydroxide In ethanol; water for 0.25h; pH=5;

: 124750-51-2
N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / toluene / 0.75 h / 45 - 50 °C 1.2: 10 h / 60 - 70 °C 2.1: diisopropylamine; sodium hydroxide / toluene; ISOPROPYLAMIDE / 4 h / 25 - 45 °C 2.2: 8 h / 40 - 70 °C 2.3: 25 - 35 °C / pH ~ 6 - 7 3.1: hydrogenchloride; water / methanol / 1 h / 0 - 35 °C 3.2: 25 - 35 °C / pH ~ 3 - 4 View Scheme
Multi-step reaction with 4 steps 1.1: potassium carbonate / tetrabutylammomium bromide / acetone / 15 h / 50 - 55 °C 2.1: potassium carbonate; water / acetone / 16 h / 20 °C 3.1: potassium carbonate; potassium iodide / acetone / 3 h / 50 - 55 °C 4.1: hydrogenchloride; water / toluene / 3 h / 20 °C 4.2: 15 - 20 °C / pH 4.5 - 5.5 View Scheme
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / dimethyl sulfoxide; acetone / 2.5 h / 0 - 5 °C / Reflux 2.1: sodium hydroxide / dimethyl sulfoxide; tetrahydrofuran / 2 h / 17 - 60 °C 2.2: 2.5 h / 70 °C 3.1: hydrogenchloride / acetonitrile; water / 2 h / 5 °C 3.2: pH 5.7 View Scheme

: 936114-12-4
potassium 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate

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

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl acetamide / 3 h / 0 - 45 °C 2: hydrogenchloride; water / methanol; ethyl acetate / 2 h / 20 °C View Scheme

: 98-88-4
benzoyl chloride

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: triethylamine / tetrahydrofuran / 3 h / 2 - 35 °C 2.1: phosphorus pentachloride / dichloromethane / 3 h / -15 - 21 °C 2.2: 4.5 h / -8 - 30 °C 3.1: triphenylphosphine; potassium carbonate; potassium bis(2-ethyl-n-hexyl)phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / 1-methyl-pyrrolidin-2-one / 8.5 h / 138 - 140 °C / Inert atmosphere 4.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C 5.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C 6.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C 7.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C 8.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C 9.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 9.2: 12 h / 45 - 50 °C 10.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 3 h / 2 - 35 °C
2.1: phosphorus pentachloride / dichloromethane / 3 h / -15 - 21 °C
2.2: 4.5 h / -8 - 30 °C
3.1: triphenylphosphine; potassium carbonate; potassium bis(2-ethyl-n-hexyl)phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / 1-methyl-pyrrolidin-2-one / 8.5 h / 138 - 140 °C / Inert atmosphere
4.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C
5.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C
6.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C
7.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C
8.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C
9.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C
9.2: 12 h / 45 - 50 °C
10.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C
View Scheme

: 1485-70-7
N-benzylbenzamide

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: phosphorus pentachloride / dichloromethane / 3 h / -15 - 21 °C 1.2: 4.5 h / -8 - 30 °C 2.1: triphenylphosphine; potassium carbonate; potassium bis(2-ethyl-n-hexyl)phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / 1-methyl-pyrrolidin-2-one / 8.5 h / 138 - 140 °C / Inert atmosphere 3.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C 4.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C 5.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C 6.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C 7.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C 8.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 8.2: 12 h / 45 - 50 °C 9.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: phosphorus pentachloride / dichloromethane / 3 h / -15 - 21 °C
1.2: 4.5 h / -8 - 30 °C
2.1: triphenylphosphine; potassium carbonate; potassium bis(2-ethyl-n-hexyl)phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / 1-methyl-pyrrolidin-2-one / 8.5 h / 138 - 140 °C / Inert atmosphere
3.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C
4.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C
5.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C
6.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C
7.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C
8.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C
8.2: 12 h / 45 - 50 °C
9.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C
View Scheme

: 28386-90-5
1-benzyl-5-phenyl-1H-tetrazole

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: triphenylphosphine; potassium carbonate; potassium bis(2-ethyl-n-hexyl)phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / 1-methyl-pyrrolidin-2-one / 8.5 h / 138 - 140 °C / Inert atmosphere 2.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C 3.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C 4.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C 5.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C 6.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C 7.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 7.2: 12 h / 45 - 50 °C 8.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme
Multi-step reaction with 8 steps 1: triphenylphosphine; potassium carbonate; [RhCl2(p-cymene)]2; potassium bis(2-ethyl-n-hexyl)phosphate / 1-methyl-pyrrolidin-2-one / 138 - 140 °C / Inert atmosphere 2: acetic acid; hydrogen bromide / 18 h / 0 - 30 °C 3: potassium carbonate / acetonitrile / 18 h / 84 °C 4: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C 5: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C 6: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C 7: potassium iodide / butanone / 20 h / 50 °C 8: acetic acid / water / 1 h / 25 °C View Scheme
Multi-step reaction with 8 steps 1: triphenylphosphine; potassium carbonate; [RhCl2(p-cymene)]2; potassium bis(2-ethyl-n-hexyl)phosphate / 1-methyl-pyrrolidin-2-one / 12 h / 138 °C / Inert atmosphere 2: 2,2'-azobis(isobutyronitrile); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / ethyl acetate / 6 h / Reflux 3: potassium carbonate / acetonitrile / 18 h / 84 °C 4: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C 5: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C 6: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C 7: potassium iodide / butanone / 20 h / 50 °C 8: acetic acid / water / 1 h / 25 °C View Scheme

: 38612-13-4
4-bromobenzyl benzoate

: 144689-63-4
olmesartan medoxomil

Conditions

Yield

Multi-step reaction with 8 steps
1.1: triphenylphosphine; potassium carbonate; potassium bis(2-ethyl-n-hexyl)phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 / 1-methyl-pyrrolidin-2-one / 8.5 h / 138 - 140 °C / Inert atmosphere
2.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C
3.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C
4.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C
5.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C
6.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C
7.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C
7.2: 12 h / 45 - 50 °C
8.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C
View Scheme

Multi-step reaction with 8 steps
1: triphenylphosphine; potassium carbonate; [RhCl2(p-cymene)]2; potassium bis(2-ethyl-n-hexyl)phosphate / 1-methyl-pyrrolidin-2-one / 138 - 140 °C / Inert atmosphere
2: acetic acid; hydrogen bromide / 18 h / 0 - 30 °C
3: potassium carbonate / acetonitrile / 18 h / 84 °C
4: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C
5: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C
6: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C
7: potassium iodide / butanone / 20 h / 50 °C
8: acetic acid / water / 1 h / 25 °C
View Scheme

: {2'-(1-benzyl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl}methyl benzoate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C 2.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C 3.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C 4.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C 5.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C 6.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 6.2: 12 h / 45 - 50 °C 7.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme
Multi-step reaction with 7 steps 1: acetic acid; hydrogen bromide / 18 h / 0 - 30 °C 2: potassium carbonate / acetonitrile / 18 h / 84 °C 3: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C 4: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C 5: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C 6: potassium iodide / butanone / 20 h / 50 °C 7: acetic acid / water / 1 h / 25 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: hydrogen bromide / acetic acid / 18.25 h / 0 - 30 °C
2.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C
3.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C
4.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C
5.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C
6.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C
6.2: 12 h / 45 - 50 °C
7.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C
View Scheme

Multi-step reaction with 7 steps
1: acetic acid; hydrogen bromide / 18 h / 0 - 30 °C
2: potassium carbonate / acetonitrile / 18 h / 84 °C
3: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C
4: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C
5: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C
6: potassium iodide / butanone / 20 h / 50 °C
7: acetic acid / water / 1 h / 25 °C
View Scheme

: 1-benzyl-5-[4'-(bromomethyl)biphenyl-2-yl]-1H-tetrazole

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C 2.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C 3.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C 4.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C 5.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 5.2: 12 h / 45 - 50 °C 6.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate / acetonitrile / 18 h / 84 °C 2: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C 3: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C 4: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C 5: potassium iodide / butanone / 20 h / 50 °C 6: acetic acid / water / 1 h / 25 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: potassium carbonate; tetrabutylammomium bromide / acetone / 20.25 h / 0 - 45 °C
2.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C
3.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C
4.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C
5.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C
5.2: 12 h / 45 - 50 °C
6.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C
View Scheme

Multi-step reaction with 6 steps
1: potassium carbonate / acetonitrile / 18 h / 84 °C
2: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C
3: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C
4: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C
5: potassium iodide / butanone / 20 h / 50 °C
6: acetic acid / water / 1 h / 25 °C
View Scheme

: ethyl 4-(1-hydroxy-1-methylethyl)-1-({2′-[1-(phenylmethyl)-1H-tetrazol-5-yl][1,1′-biphenyl]-4-yl}methyl)-2-propyl-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C 2.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C 3.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C 4.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 4.2: 12 h / 45 - 50 °C 5.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme
Multi-step reaction with 5 steps 1: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C 2: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C 3: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C 4: potassium iodide / butanone / 20 h / 50 °C 5: acetic acid / water / 1 h / 25 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 12 h / 55 - 60 °C
2.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C
3.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C
4.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C
4.2: 12 h / 45 - 50 °C
5.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C
View Scheme

Multi-step reaction with 5 steps
1: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C
2: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C
3: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C
4: potassium iodide / butanone / 20 h / 50 °C
5: acetic acid / water / 1 h / 25 °C
View Scheme

: 144689-23-6
ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{[2′-(1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 15.5 h / 0 - 30 °C 2.1: potassium hydroxide; water / acetone / 5.25 h / 0 - 45 °C 3.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 3.2: 12 h / 45 - 50 °C 4.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C 2: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C 3: potassium iodide / butanone / 20 h / 50 °C 4: acetic acid / water / 1 h / 25 °C View Scheme

: 936114-12-4
potassium 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium carbonate; potassium iodide / acetone / 0.17 h / 25 - 30 °C 1.2: 12 h / 45 - 50 °C 2.1: sulfuric acid / acetic acid; water / 1 h / 25 - 30 °C View Scheme
Multi-step reaction with 2 steps 1: potassium iodide / butanone / 20 h / 50 °C 2: acetic acid / water / 1 h / 25 °C View Scheme

: 106-38-7
para-bromotoluene

: 144689-63-4
olmesartan medoxomil

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: triphenylphosphine; potassium carbonate; [RhCl2(p-cymene)]2; potassium bis(2-ethyl-n-hexyl)phosphate / 1-methyl-pyrrolidin-2-one / 12 h / 138 °C / Inert atmosphere 2: 2,2'-azobis(isobutyronitrile); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / ethyl acetate / 6 h / Reflux 3: potassium carbonate / acetonitrile / 18 h / 84 °C 4: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C 5: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C 6: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C 7: potassium iodide / butanone / 20 h / 50 °C 8: acetic acid / water / 1 h / 25 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: triphenylphosphine; potassium carbonate; [RhCl2(p-cymene)]2; potassium bis(2-ethyl-n-hexyl)phosphate / 1-methyl-pyrrolidin-2-one / 12 h / 138 °C / Inert atmosphere
2: 2,2'-azobis(isobutyronitrile); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / ethyl acetate / 6 h / Reflux
3: potassium carbonate / acetonitrile / 18 h / 84 °C
4: 5% palladium on barium sulphate; sodium formate / water; isopropyl alcohol / 4 h / 55 °C
5: triethylamine / dichloromethane / 4.5 h / 0 - 25 °C
6: potassium hydroxide / isopropyl alcohol / 4 h / 40 °C
7: potassium iodide / butanone / 20 h / 50 °C
8: acetic acid / water / 1 h / 25 °C
View Scheme

: 144689-63-4
olmesartan medoxomil

: 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylic acid dipotassium salt

Conditions

Conditions	Yield
With water; sodium hydroxide In methanol at 20℃; for 24h;	96%

: 144689-63-4
olmesartan medoxomil

: olmesartan

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 20 - 30℃; for 20h;	90%
In water for 24h; Reflux;	88%
With water for 24h; Reflux;	88%
With Bis(p-nitrophenyl) phosphate In dimethyl sulfoxide; acetonitrile at 37℃; for 0.0333333h; pH=7.4; Reagent/catalyst; Enzymatic reaction;

: 67-56-1
methanol

: 144689-63-4
olmesartan medoxomil

: 1039762-40-7
4-(1-methoxy-1-methylethyl)-2-propyl-1-{4-(2-tetrazol-5-yl) phenyl}phenylmethylimidazole-5-carboxylic acid

Conditions

Conditions	Yield
for 24h; Reflux;	85%
for 24h; Reflux;	85%
for 24h; Reflux;	85%

: 824-94-2
p-methoxybenzyl chloride

: 144689-63-4
olmesartan medoxomil

: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-1-({2'-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-2-propyl-1H-imidazole-5-carboxylate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium carbonate In chloroform; water at 10 - 55℃; for 11h;	20.6%

: 144689-63-4
olmesartan medoxomil

: olmesartan medoxomil hemihydrate

Conditions

Conditions	Yield
With water In dimethyl sulfoxide at 20℃;

: 144689-63-4
olmesartan medoxomil

: 879562-26-2
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl1-((2'-(1H-tetrazol-5-yl) biphenyl-4-yl)methyl)-4-(prop-1-en-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions

Conditions	Yield
Stage #1: olmesartan medoxomil With sulfuric acid In ISOPROPYLAMIDE at 100℃; for 2.5h; Inert atmosphere; Stage #2: With sodium hydroxide In dichloromethane; ISOPROPYLAMIDE; water at 40℃; pH=4.2;

: 144689-63-4
olmesartan medoxomil

: 1039762-40-7
4-(1-methoxy-1-methylethyl)-2-propyl-1-{4-(2-tetrazol-5-yl) phenyl}phenylmethylimidazole-5-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 24 h / Reflux 2: 24 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: water / 24 h / Reflux 2: 24 h / Reflux View Scheme

: 144689-63-4
olmesartan medoxomil

A: 1039762-40-7
4-(1-methoxy-1-methylethyl)-2-propyl-1-{4-(2-tetrazol-5-yl) phenyl}phenylmethylimidazole-5-carboxylic acid

B: olmesartan methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 24 h / Reflux 2: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 5 h / 20 °C View Scheme

Olmesartan medoxomil Chemical Properties

Molecular Structure of Olmesartan medoxomil (CAS NO.144689-63-4):

IUPAC Name: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate
Molecular formula: C₂₉H₃₀N₆O₆
Molecular Weight: 558.5851
H bond acceptors: 12
H bond donors: 2
Freely Rotating Bonds: 12
Polar Surface Area: 132.48Å²
Index of Refraction: 1.661
Molar Refractivity: 149.19 cm³
Molar Volume: 403.5 cm³
Surface Tension: 53.6 dyne/cm
Density: 1.38 g/cm³
Flash Point: 440.2 °C
Enthalpy of Vaporization: 122.61 kJ/mol
Boiling Point: 804.2 °C at 760 mmHg
Vapour Pressure: 2.63E-27 mmHg at 25°C
Melting point: 180°C
Decomposition: 180 ^oC
Appearance: White to off-white crystalline powder
InChI
InChI=1/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34)
Smiles
c1(n(Cc2ccc(cc2)c2ccccc2c2nnn[nH]2)c(C(=O)OCc2oc(oc2C)=O)c(n1)C(C)(O)C)CCC
Product Categories: Active Pharmaceutical Ingredients; Aromatics; Bases & Related Reagents; Heterocycles; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals; Olmesartan

Olmesartan medoxomil Specification

Olmesartan medoxomil , with CAS number of 144689-63-4, can be called 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2(1H-tetazol-5-yl)[1,1biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester ; Oimesartan ; 4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl-1H-Imidazole-5-carboxylic acid, (5-methyl -2-oxo-1,3-dioxol-4-yl) methyl ester ; Benicar . Olmesartan medoxomil is an angiotensin II receptor antagonist. It is used as an anti-hypertensive.

Product Name

Olmesartan medoxomil

Synthetic route

Olmesartan medoxomil Chemical Properties

Olmesartan medoxomil Specification

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