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| CAS No.: | 138402-11-6 |
|---|---|
| Name: | Irbesartan |
| Article Data: | 57 |
| Molecular Structure: | |
|
|
|
| Formula: | C25H28N6O |
| Molecular Weight: | 428.537 |
| Synonyms: | BMS 186295;SR 47436;2-Butyl-3-(p-(o-1H-tetrazol-5-ylphenyl)benzyl)-1,3-diazaspiro(4.4)non-1-en-4-one;1,3-Diazaspiro[4.4]non-1-en-4-one,2-butyl- 3-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]- methyl]-;Avapro;3-byty1-3-[p-(0-1H-tetrazol-5-y1-pheny1)benzy1],3-diazospiro[4,4]non-1-en-4-ketone;Aprovel;138402-11-6;Irbesartan (JAN/USAN);Avapro (TN); |
| EINECS: | 604-078-2 |
| Density: | 1.3 g/cm3 |
| Melting Point: | 180-181 °C |
| Boiling Point: | 648.6 °C at 760 mmHg |
| Flash Point: | 346 °C |
| Appearance: | white crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 26 |
| PSA: | 87.13000 |
| LogP: | 4.15090 |
- 144851-82-1METHYL2-AMINO-3-FLUOROBENZOATE
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- 5156-58-1N-(1-Benzyl-4-pipperidinyl)-N-phenylpropanamide HCl
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- 50288-62-5threo-Phenyl-2-piperidyl acetamide
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 47087-37-6Z-D-Glu-OMe
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 25 - 55℃; for 3.5h; | 100% |
| In water; isopropyl alcohol at 55℃; for 6h; | 96% |
| With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 55℃; for 3.5h; Time; | 0.091 g |
- 138402-10-5
trityl irbesartan
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| Stage #1: trityl irbesartan With hydrogenchloride In water; acetone at 35 - 45℃; for 1.5 - 2h; Stage #2: In water; acetone at 15℃; pH=11 - 13; Alkaline aqueous solution; | 98.75% |
| With sulfuric acid In water; acetone at 35 - 40℃; for 7h; | 93% |
| With sodium hydroxide In methanol at 20℃; | 87% |
- 138401-24-8
4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| With sodium azide; tributyltin chloride In o-xylene Heating; | 95% |
| With sodium azide; triethylamine hydrochloride In toluene at 100℃; for 24h; Solvent; Temperature; Large scale; | 90% |
| With trimethylsilylazide; tetrabutyl ammonium fluoride In water; N,N-dimethyl-formamide at 120℃; for 36h; | 89% |
- 124750-51-2
N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| Stage #1: N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole; 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride With sodium hydroxide; tetrabutylammomium bromide In water; toluene at 85℃; for 2h; Stage #2: With hydrogenchloride; water In acetone at 20℃; Stage #3: With potassium hydroxide In water; acetone Product distribution / selectivity; | 92% |
| With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 90℃; for 1.5h; Heating / reflux; | 84.3% |
| Stage #1: N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole; 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 90℃; for 1.5h; Stage #2: With hydrogenchloride; water In acetone at 20℃; Stage #3: With potassium hydroxide In water; acetone Product distribution / selectivity; | 84% |
| Stage #1: N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole; 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride With tetrabutylammomium bromide; potassium carbonate In ethyl acetate at 25 - 80℃; for 10h; Stage #2: With hydrogenchloride In methanol at 0 - 30℃; for 3.5h; Stage #3: With sodium hydroxide In water; toluene at 0 - 30℃; for 0.5h; pH=12; |
- 138402-10-5
trityl irbesartan
A
- 596-31-6
methoxytriphenylmethane
B
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| Stage #1: trityl irbesartan With hydroxylamine hydrochloride In methanol; water; acetone at 20℃; for 2h; Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=3.8 - 12.5; | A n/a B 91% |
| Stage #1: trityl irbesartan With hydroxylamine hydrochloride In methanol; water; isopropyl alcohol; acetone at 20℃; for 2h; Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=12.0 - 12.5; | A n/a B 89% |
- 141745-71-3
1-pentanoylamino-cyclopentanecarboxylic acid (2'-cyano-biphenyl-4-ylmethyl)-amide
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| Stage #1: 1-pentanoylamino-cyclopentanecarboxylic acid (2'-cyano-biphenyl-4-ylmethyl)-amide With sodium azide; tributyltin chloride; N,N-dimethyl-formamide In o-xylene at 15 - 155℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; o-xylene; water at 20℃; for 1h; Product distribution / selectivity; | 90% |
| With sodium azide; tributyltin chloride; N,N-dimethyl-formamide In o-xylene at 150 - 155℃; for 20h; | 71% |
| Multi-step reaction with 2 steps 1: 81 percent / trifluoro acetic acid / toluene / Heating 2: 95 percent / tributyl tin chloride; sodium azide / o-xylene / Heating View Scheme |
- 945540-18-1
4-[(α-N-pentanoylamino)cyclopentamidomethyl]-2'-carboxamidobiphenyl
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| Stage #1: 4-[(α-N-pentanoylamino)cyclopentamidomethyl]-2'-carboxamidobiphenyl With sodium azide; tributyltin chloride; N,N-dimethyl-formamide In o-xylene at 15 - 155℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; o-xylene; water at 20 - 25℃; for 1.5h; Product distribution / selectivity; | 88.5% |
| With sodium azide; tributyltin chloride; N,N-dimethyl-formamide for 50h; | 65% |
| Multi-step reaction with 2 steps 1: 65 percent / trifluoroacetic acid / o-xylene / 17 h / Heating 2: 80 percent / sodium azide; tributyltin chloride; DMF / o-xylene / 40 h / 150 - 155 °C View Scheme | |
| Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / o-xylene / 15 h / 25 - 140 °C 1.2: 0.17 h / 25 - 30 °C / pH 9 2.1: sodium azide; tributyltin chloride / o-xylene / 25 °C / Heating / reflux 2.2: 2.25 h / 20 - 25 °C 2.3: 2 h / 20 - 25 °C / pH 4.5 - 4.8 View Scheme | |
| Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / o-xylene / 15 h / 25 - 140 °C 1.2: 0.17 h / 25 - 30 °C / pH 9 2.1: pyridine; p-toluenesulfonyl chloride / 1 h / 70 - 75 °C 3.1: sodium azide; tributyltin chloride / o-xylene / 60 h / 25 - 137 °C 3.2: 1 h / 10 - 15 °C / pH 11.5 - 12 3.3: 10 - 30 °C / pH 4.6 - 4.8 View Scheme |
- 731851-41-5
3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one
- 144873-97-2
2-(N-triphenylmethyl-tetrazol-5-yl)-phenylboronic acid
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In methanol for 10h; Suzuki coupling; Heating; | 84% |
| Stage #1: 3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one; 2-(N-triphenylmethyl-tetrazol-5-yl)-phenylboronic acid With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 25 - 85℃; for 0.5h; Stage #2: With hydrogenchloride In water; 4-methyl-2-pentanone Product distribution / selectivity; | 22% |
- 1199814-92-0
3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2-thiophen-2-yl-1,3-diaza-spiro[4.4]non-1-en-4-one
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| With hydrogen; Raney nickel In methanol at 20℃; | 84% |
- 144625-34-3
1-[(2'-carboxamidobiphenyl-4-yl)methyl]-2-n-butyl-4-spirocyclopentane-2-imidazolin-5-one
- 138402-11-6
2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one
| Conditions | Yield |
|---|---|
| With sodium azide; tributyltin chloride; N,N-dimethyl-formamide In o-xylene at 150 - 155℃; for 40h; | 80% |
| Stage #1: 1-[(2'-carboxamidobiphenyl-4-yl)methyl]-2-n-butyl-4-spirocyclopentane-2-imidazolin-5-one With sodium azide; tributyltin chloride In o-xylene at 25℃; Heating / reflux; Stage #2: With hydrogenchloride In dichloromethane; o-xylene; water at 20 - 25℃; for 2.25h; Stage #3: With ammonia In dichloromethane; o-xylene; water at 20 - 25℃; for 2h; pH=4.5 - 4.8; Product distribution / selectivity; | 77% |
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Chemistry
Molecular Structure of Irbesartan (CAS NO.138402-11-6):
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IUPAC Name: 2-butyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one
Empirical Formula: C25H28N6O
Molecular Weight: 428.5294
H bond acceptors: 7
H bond donors: 1
Freely Rotating Bonds: 7
Polar Surface Area: 76.27 Å2
Index of Refraction: 1.689
Molar Refractivity: 125.44 cm3
Molar Volume: 328.2 cm3
Surface Tension: 54.4 dyne/cm
Density: 1.3 g/cm3
Flash Point: 346 °C
Enthalpy of Vaporization: 95.62 kJ/mol
Boiling Point: 648.6 °C at 760 mmHg
Vapour Pressure: 1.05E-16 mmHg at 25°C
Melting point: 180-181°C
InChI
InChI=1/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)
Smiles
C12(C(N(Cc3ccc(c4c(c5[nH]nnn5)cccc4)cc3)C(=N1)CCCC)=O)CCCC2
Product Categories: Active Pharmaceutical Ingredients; Antihypertensive; Hypertension; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; API's
Safety Profile
Hazard Codes: 
Xn
Risk Statements: 22
R22:Harmful if swallowed.
Safety Statements: 26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Specification
Irbesartan , with CAS number of 138402-11-6, can be called 1,3-Diazaspiro(4.4)non-1-en-4-one, 2-butyl-3-((2-(1H-tetrazol-5-yl)(1,1-biphenyl)-4-yl)methyl)- ; 1,3-Diazaspiro[4.4]non-1-en-4-one,2-butyl- 3-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]- methyl]- ; Avapro ; 3-byty1-3-[p-(0-1H-tetrazol-5-y1-pheny1)benzy1],3-diazospiro[4,4]non-1-en-4-ketone ; 2-Butyl-3-(p-(o-1H-tetrazol-5-ylphenyl)benzyl)-1,3-diazaspiro(4.4)non-1-en-4-one . It is a crystalline solid, used as an angiotensin II type 1 (AII1)-receptor antagonist. Irbesartan is also available in a combination formulation with a low dose thiazide diuretic, invariably Hydrochlorothiazide, to achieve an additive antihypertensive effect.