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Azilsartan

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Name

Azilsartan

EINECS 808-058-6
CAS No. 147403-03-0 Density 1.42 cm3
PSA 123.24000 LogP 4.19180
Solubility N/A Melting Point 188 °C(dec.)
Formula C25H20N4O5 Boiling Point N/A
Molecular Weight 456.458 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 147403-03-0 (Azilsartan) Hazard Symbols N/A
Synonyms

see 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-;TAK 536;2-Ethoxy-1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid;

Article Data 35

Azilsartan Synthetic route

1403474-70-3

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

147403-03-0

azilsartan

Conditions
ConditionsYield
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%

C25H19N4O5(1-)*Na(1+)

147403-03-0

azilsartan

Conditions
ConditionsYield
With citric acid In water at 5℃; pH=5; Reagent/catalyst;97.1%
147403-52-9

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

147403-03-0

azilsartan

Conditions
ConditionsYield
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%

C25H19N4O5(1-)*K(1+)

147403-03-0

azilsartan

Conditions
ConditionsYield
With citric acid In water at 5℃; pH=5; Reagent/catalyst;96.7%
0.36N-NaOH

0.36N-NaOH

7440-44-0

pyrographite

147403-52-9

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

147403-03-0

azilsartan

Conditions
ConditionsYield
96%
0.40N-NaOH

0.40N-NaOH

7440-44-0

pyrographite

147403-52-9

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

147403-03-0

azilsartan

Conditions
ConditionsYield
96%

C25H19N4O5(1-)*Li(1+)

147403-03-0

azilsartan

Conditions
ConditionsYield
With citric acid In water at 5℃; pH=5; Reagent/catalyst;95.8%
863031-21-4

Azilsartan medoxomil

147403-03-0

azilsartan

Conditions
ConditionsYield
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;

2-ethoxy-1-[[2′-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid ethyl ester di-n-butylamine

147403-03-0

azilsartan

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 45 - 56℃; for 2.5h;93%

C28H28N4O5

147403-03-0

azilsartan

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 40 - 50℃; for 1h; Reagent/catalyst;92.8%

Azilsartan Specification

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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