ethyl ester of 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
azilsartan
Conditions | Yield |
---|---|
With water; sodium hydroxide at 50℃; for 4h; | 98.5% |
With sodium hydroxide In water at 70 - 75℃; for 1.5h; Temperature; | 93.4% |
With pyrographite; sodium hydroxide In water at 55℃; for 2h; Temperature; | 91% |
azilsartan
Conditions | Yield |
---|---|
With citric acid In water at 5℃; pH=5; Reagent/catalyst; | 97.1% |
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
azilsartan
Conditions | Yield |
---|---|
Stage #1: 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 With water; sodium hydroxide In methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In water Product distribution / selectivity; | 96.4% |
With sodium hydroxide In methanol; water at 20℃; for 24h; | 96% |
With sodium hydroxide In water at 60 - 65℃; Temperature; | 96.8% |
azilsartan
Conditions | Yield |
---|---|
With citric acid In water at 5℃; pH=5; Reagent/catalyst; | 96.7% |
pyrographite
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
azilsartan
Conditions | Yield |
---|---|
96% |
pyrographite
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
azilsartan
Conditions | Yield |
---|---|
96% |
azilsartan
Conditions | Yield |
---|---|
With citric acid In water at 5℃; pH=5; Reagent/catalyst; | 95.8% |
Azilsartan medoxomil
azilsartan
Conditions | Yield |
---|---|
With water; sodium hydroxide at 75℃; for 1h; Temperature; Reagent/catalyst; | 94.84% |
With Bis(p-nitrophenyl) phosphate In acetonitrile at 37℃; for 0.0833333h; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction; |
azilsartan
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol at 45 - 56℃; for 2.5h; | 93% |
azilsartan
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 40 - 50℃; for 1h; Reagent/catalyst; | 92.8% |
ethyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
chloroformic acid ethyl ester
azilsartan
Conditions | Yield |
---|---|
Stage #1: ethyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate; chloroformic acid ethyl ester With triethylamine In toluene at 30℃; for 2h; Stage #2: With dmap; water In toluene for 3h; Reflux; | 89% |
2-ethoxy-1-[[2'-[N'((ethoxycarbonyl)oxy)carbamimidoyl][1,1-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid methyl ester
azilsartan
Conditions | Yield |
---|---|
With sodium hydroxide In water at 40℃; for 2h; Reagent/catalyst; Temperature; | 87% |
Multi-step reaction with 2 steps 1.1: xylene / 1.5 h / Reflux 2.1: sodium hydroxide; water / 1.5 h / 70 °C 2.2: pH 3 View Scheme | |
Multi-step reaction with 2 steps 1: xylene / 1.5 h / Reflux 2: sodium hydroxide; water / methanol / 24 h / 20 °C View Scheme |
methyl 2-ethoxy-1-((2'-(N'-(phenoxycarbonyloxy)carbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
With water; sodium hydroxide at 100℃; for 3h; Reagent/catalyst; | 84% |
Multi-step reaction with 2 steps 1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 1 h / 20 °C 2.1: sodium hydroxide; water / 1.5 h / 70 °C 2.2: pH 3 View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C 2: sodium hydroxide / water; methanol / 24 h / 20 °C View Scheme |
1-[(2'-(N'-hydroxycarbamimidoyl)[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-1,3-benzodiazole-7-carboxylic acid
phenyl chloroformate
azilsartan
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 3h; Reagent/catalyst; Solvent; | 82% |
1-[(2'-(N'-hydroxycarbamimidoyl)[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-1,3-benzodiazole-7-carboxylic acid
methyl chloroformate
azilsartan
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 3h; | 80% |
carbonic acid dimethyl ester
methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
Stage #1: carbonic acid dimethyl ester; methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 4h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide Product distribution / selectivity; | 78.9% |
1-[(2'-(N'-hydroxycarbamimidoyl)[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-1,3-benzodiazole-7-carboxylic acid
isopropyl chloroformate
azilsartan
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 3h; | 78% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -70℃; Inert atmosphere; | 71% |
methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 55 percent / hydroxylamine / dimethylsulfoxide / 15 h / 75 °C 2: pyridine / dimethylformamide / 0.5 h / 0 °C 3: xylene / 2 h / Heating 4: 94 percent / 0.4 N aq. NaOH / 1.5 h / 70 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / dimethyl sulfoxide / 18 h / 25 - 90 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 - 25 °C 3.1: sodium hydroxide; water / 0.5 h / 50 - 55 °C 3.2: 0.5 h / 20 - 25 °C / pH 2 - 3 View Scheme | |
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / dimethyl sulfoxide; water / 18 h / 90 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 4 h / 20 °C 3: sodium hydroxide; water / 3 h / 50 °C View Scheme |
methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine / dimethylformamide / 0.5 h / 0 °C 2: xylene / 2 h / Heating 3: 94 percent / 0.4 N aq. NaOH / 1.5 h / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 - 25 °C 2.1: sodium hydroxide; water / 0.5 h / 50 - 55 °C 2.2: 0.5 h / 20 - 25 °C / pH 2 - 3 View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane; tetrahydrofuran / 2 h / 20 °C / Cooling with water-ice 2.1: xylene / 1.5 h / Reflux 3.1: sodium hydroxide; water / 1.5 h / 70 °C 3.2: pH 3 View Scheme |
azilsartan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: xylene / 2 h / Heating 2: 94 percent / 0.4 N aq. NaOH / 1.5 h / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: xylene / 2 h / Reflux 2.1: sodium hydroxide; water / 1.5 h / 70 °C 2.2: pH 3 View Scheme | |
Multi-step reaction with 2 steps 1: xylene / 2 h / Reflux 2: sodium hydroxide; water / methanol / 24 h / 20 °C View Scheme |
chloroformic acid ethyl ester
methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
Stage #1: chloroformic acid ethyl ester; methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate With pyridine In N,N-dimethyl-formamide for 6h; Inert atmosphere; Cooling with ice-cold bath; Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 5h; Stage #3: With hydrogenchloride In water; dimethyl sulfoxide |
methyl 2-ethoxy-1-((2'-(N'-(methoxycarbonyloxy)carbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
With sodium methylate In tetrahydrofuran at 20℃; for 4h; | 71.2 %Chromat. |
Multi-step reaction with 2 steps 1.1: sodium methylate / 1-methyl-pyrrolidin-2-one / 4 h / 20 °C 2.1: sodium hydroxide; water / 1.5 h / 70 °C 2.2: pH 3 View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 20 °C 2.1: pyridine / N,N-dimethyl-formamide / 6 h / Inert atmosphere; Cooling with ice-cold bath 2.2: 5 h / 20 °C View Scheme |
methyl 2-ethoxy-1-((2'-(N'-(methoxycarbonyloxy)carbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
A
azilsartan
B
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
Conditions | Yield |
---|---|
With sodium methylate In 1-methyl-pyrrolidin-2-one at 20℃; for 4h; | A 11.3 %Chromat. B 72.7 %Chromat. |
With sodium methylate In dimethyl sulfoxide at 20℃; for 4h; | A 77.9 %Chromat. B 17.1 %Chromat. |
methyl 2-ethoxy-1-((2'-(N'-(methoxycarbonyloxy)carbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
A
methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
B
azilsartan
Conditions | Yield |
---|---|
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 20℃; for 4h; Product distribution / selectivity; | A 7.9 %Chromat. B 74.8 %Chromat. |
ethyl 2-ethoxy-1-((2'-(N'-((ethoxycarbonyl)oxy)carbamimidoyl)[biphenyl]-4-yl)methyl)-1H-benzoimidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
With sodium ethanolate In tetrahydrofuran at 20℃; for 4h; | 66 %Chromat. |
With potassium tert-butylate In tetrahydrofuran at 20℃; for 4h; Product distribution / selectivity; | 93 %Chromat. |
Multi-step reaction with 2 steps 1: dibutylamine / 2 h / 110 - 115 °C 2: sodium hydroxide; water / 1.5 h / 70 - 75 °C View Scheme | |
Multi-step reaction with 2 steps 1: isopropyl alcohol / 80 °C 2: pyrographite; sodium hydroxide / water / 2 h / 55 °C View Scheme |
ethyl 2-ethoxy-1-((2'-(N'-((ethoxycarbonyl)oxy)carbamimidoyl)[biphenyl]-4-yl)methyl)-1H-benzoimidazole-7-carboxylate
A
ethyl ester of 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
B
azilsartan
Conditions | Yield |
---|---|
With sodium ethanolate In dimethyl sulfoxide at 20℃; for 4h; Product distribution / selectivity; | A 39.3 %Chromat. B 55.3 %Chromat. |
ethyl 1-[(2'-cyano-[1,1']-biphenyl-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / dimethyl sulfoxide; water / 15 h / 90 °C 2: dimethyl sulfoxide; methanol / 2 h / 20 - 25 °C 3: sodium hydroxide; water / 3 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine; hydroxylamine hydrochloride / dimethyl sulfoxide / 12 h / 75 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / 20 °C 3: sodium hydroxide / 75 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine; hydroxylamine / ethanol; water / 7 h 2: triethylamine / dichloromethane / 2 h / 20 °C 3: ethanol / 15 h / Reflux 4: sodium hydroxide / ethanol / 1.6 h / 73 - 75 °C View Scheme |
ethyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate
azilsartan
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethyl sulfoxide; methanol / 2 h / 20 - 25 °C 2: sodium hydroxide; water / 3 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: ethanol / 15 h / Reflux 3: sodium hydroxide / ethanol / 1.6 h / 73 - 75 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: ethanol / 15 h / Reflux 3: sodium hydroxide / ethanol / 1.6 h / 73 - 75 °C View Scheme |
azilsartan
Conditions | Yield |
---|---|
With palladium on activated charcoal; ammonium formate; acetic acid In ethanol at 80℃; for 5h; Inert atmosphere; | 96% |
4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one
azilsartan
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% |
3-(hydroxymethyl)-4-phenylfuroxan
azilsartan
Conditions | Yield |
---|---|
With dmap; triethylamine; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 5h; Reagent/catalyst; Solvent; Temperature; | 94% |
With dmap; potassium carbonate; p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 10℃; for 3h; |
N,N-dimethyl acetamide
4-hydroxymethyl-5-methyl-[1,3]dioxol-2-one
azilsartan
(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
Conditions | Yield |
---|---|
With dmap; potassium carbonate; p-toluenesulfonyl chloride at 30℃; for 3h; Cooling; | 86.4% |
Conditions | Yield |
---|---|
With sodium carbonate; sodium iodide In N,N-dimethyl acetamide at 35℃; for 3h; Reagent/catalyst; Solvent; | 85.9% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h; | 83% |
Conditions | Yield |
---|---|
With sodium carbonate In tetrahydrofuran at 70 - 80℃; for 6h; Reagent/catalyst; Solvent; | 78.4% |
azilsartan
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 20℃; for 3h; pH=2; | 60% |
With hydrogen bromide In ethanol at 78 - 85℃; for 1h; |
Conditions | Yield |
---|---|
In water at 20℃; for 2h; | 45% |
azilsartan
2-oxo-4-hydroxymethyl-3-methyl-1,2,5-oxadiazol
Conditions | Yield |
---|---|
With dmap; potassium carbonate; p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 20℃; for 3h; | 44.4% |
With dmap; potassium carbonate; p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 20℃; for 3h; | 44.4% |
Conditions | Yield |
---|---|
In water at 20℃; for 2h; | 44% |
The IUPAC name of Azilsartan is 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid. With the CAS registry number 147403-03-0, it is also named as 2-Ethoxy-1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid. The product's classification code is treatment of hypertension. Moreover, its molecular formula is C25H20N4O5 and its molecular weight is 456.45.
The other characteristics of Azilsartan can be summarized as: (1)XLogP3-AA: 4.4; (2)H-Bond Donor: 2; (3)H-Bond Acceptor: 7; (4)Rotatable Bond Count: 7; (5)Tautomer Count: 3; (6)Exact Mass: 456.14337; (7)MonoIsotopic Mass: 456.14337; (8)Topological Polar Surface Area: 115; (9)Heavy Atom Count: 34; (10)Complexity: 783; (11)Density: 1.42 cm3.
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NC(=O)ON5)C(=O)O
(2)InChI: InChI=1S/C25H20N4O5/c1-2-33-24-26-20-9-5-8-19(23(30)31)21(20)29(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-27-25(32)34-28-22/h3-13H,2,14H2,1H3,(H,30,31)(H,27,28,32)
(3)InChIKey: KGSXMPPBFPAXLY-UHFFFAOYSA-N
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