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Name	Irbesartan	EINECS	604-078-2
CAS No.	138402-11-6	Density	1.3 g/cm³
PSA	87.13000	LogP	4.15090
Solubility	N/A	Melting Point	180-181 °C
Formula	C₂₅H₂₈N₆O	Boiling Point	648.6 °C at 760 mmHg
Molecular Weight	428.537	Flash Point	346 °C
Transport Information	N/A	Appearance	white crystalline powder
Safety	26	Risk Codes	22
Molecular Structure		Hazard Symbols	Xn
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);	Article Data	57

Irbesartan Synthetic route

: 3-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-2-butyl-1,3-diazaspiro[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

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

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

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

: 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride

: 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

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

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

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

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

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

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

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%

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%

Irbesartan Chemical Properties

Molecular Structure of Irbesartan (CAS NO.138402-11-6):

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

Irbesartan Safety Profile

Hazard Codes: Harmful 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.

Irbesartan 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.

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