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CAS

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138402-10-5

Trityl Irbesartan, also known as 2-Butyl-3-((2''-(2-trityl-2H-tetrazol-5-yl)-[1,1''-biphenyl]-4-yl)methyl)-1,3-diazaspiro[4.4]non-1-en-4-one, is a derivative of Irbesartan (I751000). It is a chemical compound that has been specifically designed and synthesized for use in the pharmaceutical industry. Trityl Irbesartan possesses unique structural properties that make it a valuable building block in the development of antihypertensive drugs.

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  • 138402-10-5 Structure

  • Basic information

    1. Product Name: Trityl Irbesartan
    2. Synonyms: TRITYL IRBESARTAN;TRIPHENYLMETHYL IRBESARTAN;2-butyl-3-[[4-[2-(2-trityl-tetrazol-5-yl)phenyl]phenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one;Trityl Irbestartan;2-N-BUTYL-4-SPIROCYCLOPENTANE-1-[(2'-(TRIPHENYL-METHYLTETRAZOL-5-YL)BIPHENYL-4-Y;TRIPHENYL IRBESARTAN;N-TriphenylMethyl Irbesartan;Irbesartan N1-Trityl IMpurity
    3. CAS NO:138402-10-5
    4. Molecular Formula: C44H42N6O
    5. Molecular Weight: 670.84
    6. EINECS: 1312995-182-4
    7. Product Categories: Irbesartan;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 138402-10-5.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 834.612 °C at 760 mmHg
    3. Flash Point: 458.557 °C
    4. Appearance: White powder
    5. Density: 1.201 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.662
    8. Storage Temp.: Sealed in dry,Store in freezer, under -20°C
    9. Solubility: N/A
    10. PKA: 2.60±0.20(Predicted)
    11. CAS DataBase Reference: Trityl Irbesartan(CAS DataBase Reference)
    12. NIST Chemistry Reference: Trityl Irbesartan(138402-10-5)
    13. EPA Substance Registry System: Trityl Irbesartan(138402-10-5)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 138402-10-5(Hazardous Substances Data)

138402-10-5 Usage

Uses

Used in Pharmaceutical Industry:
Trityl Irbesartan is used as a building block for the development of antihypertensive drugs, specifically in the preparation of Irbesartan. It plays a crucial role in the synthesis of these medications, which are designed to help lower blood pressure and manage hypertension. The unique properties of Trityl Irbesartan contribute to the effectiveness of the final drug product, making it a valuable component in the pharmaceutical industry.

Check Digit Verification of cas no

The CAS Registry Mumber 138402-10-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,4,0 and 2 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 138402-10:
(8*1)+(7*3)+(6*8)+(5*4)+(4*0)+(3*2)+(2*1)+(1*0)=105
105 % 10 = 5
So 138402-10-5 is a valid CAS Registry Number.
InChI:InChI=1/C44H42N6O/c1-2-3-25-40-45-43(30-15-16-31-43)42(51)49(40)32-33-26-28-34(29-27-33)38-23-13-14-24-39(38)41-46-47-48-50(41)44(35-17-7-4-8-18-35,36-19-9-5-10-20-36)37-21-11-6-12-22-37/h4-14,17-24,26-29H,2-3,15-16,25,30-32H2,1H3

138402-10-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Triphenylmethyl Irbesartan

1.2 Other means of identification

Product number -
Other names 2-butyl-3-[[4-[2-(2-trityltetrazol-5-yl)phenyl]phenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:138402-10-5 SDS

138402-10-5Synthetic route

3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one
731851-41-5

3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
Stage #1: 2-(N-triphenylmethyl-tetrazol-5-yl)-phenylboronic acid; palladium diacetate; triphenylphosphine In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 0.666667h;
Stage #2: 3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one With water; potassium carbonate In tetrahydrofuran; 1,2-dimethoxyethane at 20 - 80℃; for 3.5h; Heating / reflux;		90%
N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole
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

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

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 0.0194444h; microwave irradiation;90%
2-(2-thienyl)-3-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1,3-diazaspiro[4.4]non-1-en-4-one
1199814-94-2

2-(2-thienyl)-3-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1,3-diazaspiro[4.4]non-1-en-4-one

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
With hydrogen; Raney nickel In N,N-dimethyl-formamide at 20℃;88%
3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one
731851-41-5

3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one

2-(N-triphenylmethyl-tetrazol-5-yl)-phenylboronic acid
144873-97-2

2-(N-triphenylmethyl-tetrazol-5-yl)-phenylboronic acid

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
With potassium carbonate; palladium diacetate; triphenylphosphine In water; toluene at 95 - 100℃; for 3 - 4h; Product distribution / selectivity;80%
With caesium carbonate; palladium diacetate; triphenylphosphine In water; toluene at 95 - 100℃; for 3 - 4h; Product distribution / selectivity;80%
With potassium hydroxide; palladium diacetate; triphenylphosphine In water; toluene at 95 - 100℃; for 3 - 4h; Product distribution / selectivity;72%
N-pentanoylaminocyclopentane-1-carboxylic acid
15026-80-9

N-pentanoylaminocyclopentane-1-carboxylic acid

1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine
134603-82-0

1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
Stage #1: N-pentanoylaminocyclopentane-1-carboxylic acid; 1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine With methanesulfonic acid In toluene at 20℃; for 48h; Heating / reflux;
Stage #2: With sodium hydroxide In water; ethyl acetate for 0.5h;		80%
Stage #1: N-pentanoylaminocyclopentane-1-carboxylic acid; 1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine With methanesulfonic acid In toluene at 20℃; for 48h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate for 0.5h;		80%
2-n-butyl-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-1,3-diazaspiro[4.4]non-1-ene-4-one
894806-38-3

2-n-butyl-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-1,3-diazaspiro[4.4]non-1-ene-4-one

N-trityl-5-(2-bromophenyl)tetrazole
143945-72-6

N-trityl-5-(2-bromophenyl)tetrazole

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
Stage #1: With triphenylphosphine; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 2-n-butyl-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)benzyl]-1,3-diazaspiro[4.4]non-1-ene-4-one; N-trityl-5-(2-bromophenyl)tetrazole With potassium phosphate In tetrahydrofuran for 48h; Product distribution / selectivity; Heating / reflux;		54%
With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 48h; Product distribution / selectivity; Heating / reflux;32%
1-(1'-ethoxy)pentanaminylcyclopentent carboxylate
745814-10-2

1-(1'-ethoxy)pentanaminylcyclopentent carboxylate

1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine
134603-82-0

1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
acetic acid In toluene for 3h; Heating / reflux;50%
4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenylboronic acid
894806-37-2

4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenylboronic acid

N-trityl-5-(2-bromophenyl)tetrazole
143945-72-6

N-trityl-5-(2-bromophenyl)tetrazole

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; ethyl acetate; N,N-dimethyl-formamide; toluene at 85℃; for 48h; Product distribution / selectivity;50%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene for 5 - 6h; Suzuki Coupling; Heating / reflux;
With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 6h;
1-(pentanoylamino)cyclopentanecarboxamide
177219-40-8

1-(pentanoylamino)cyclopentanecarboxamide

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

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

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate In toluene at 50 - 90℃; for 4h;32%
With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 90℃; for 1.5h;
C13H23NO3
745814-11-3

C13H23NO3

1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine
134603-82-0

1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
Stage #1: C13H23NO3 With 2,6-dimethylpyridine; oxalyl dichloride In toluene at 0℃; for 1h;
Stage #2: 1-(2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methanamine In toluene at 0 - 20℃; for 1h;		30%
N-pentanoyl-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amine
439904-79-7

N-pentanoyl-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amine

ethyl 1-aminocyclopentanecarboxylate
1664-35-3

ethyl 1-aminocyclopentanecarboxylate

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
Stage #1: N-pentanoyl-N-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]amine With 2,6-dimethylpyridine; oxalyl dichloride In toluene at 0℃; for 1h;
Stage #2: ethyl 1-aminocyclopentanecarboxylate In toluene at 0 - 20℃; for 1h;		25%
2-(1-TRITYL-1H-TETRAZOL-5-YL)-4'-(1''-ETHOXYPENTANAMINYL)BIPHENYL
745814-08-8

2-(1-TRITYL-1H-TETRAZOL-5-YL)-4'-(1''-ETHOXYPENTANAMINYL)BIPHENYL

ethyl 1-aminocyclopentanecarboxylate
1664-35-3

ethyl 1-aminocyclopentanecarboxylate

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
Stage #1: 2-(1-TRITYL-1H-TETRAZOL-5-YL)-4'-(1''-ETHOXYPENTANAMINYL)BIPHENYL; ethyl 1-aminocyclopentanecarboxylate In toluene at 20℃; for 2h;
Stage #2: acetic acid In toluene for 5h; Heating / reflux;		20%
5-(4-(bromomethyl)-[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole

5-(4-(bromomethyl)-[1,1'-biphenyl]-2-yl]-1-(triphenylmethyl)-1H-tetrazole

2-butyl-1,3-diaza-spiro[4.4]non-1-en-4one
138402-05-8

2-butyl-1,3-diaza-spiro[4.4]non-1-en-4one

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
With potassium hydroxide; tetrabutylammomium bromide In acetonitrile at 31 - 40℃; for 2.5h; Product distribution / selectivity;
trityl chloride
76-83-5

trityl chloride

4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile
138401-24-8

4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile

trityl irbesartan
138402-10-5

trityl irbesartan

Conditions
ConditionsYield
Stage #1: 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile With tributyltin azide In xylene for 66h; Heating / reflux;
Stage #2: trityl chloride With sodium hydroxide In tetrahydrofuran; dichloromethane; water for 26h;
Stage #1: 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile With sodium azide; tributyltin chloride; tetrabutylammomium bromide In toluene for 20h; Heating / reflux;
Stage #2: With acetic acid In water; toluene at 20℃; for 0.25h;
Stage #3: trityl chloride With triethylamine In dichloromethane at 25 - 30℃; for 2h;
trityl irbesartan
138402-10-5

trityl irbesartan

2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-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
ConditionsYield
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%
trityl irbesartan
138402-10-5

trityl irbesartan

2-n-butyl-4-spirocyclopentane-1-[(2'-(tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one hydrochloride sesquihydrate

2-n-butyl-4-spirocyclopentane-1-[(2'-(tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one hydrochloride sesquihydrate

Conditions
ConditionsYield
With hydrogenchloride; water In toluene at 55℃; for 1h; Product distribution / selectivity;95%
trityl irbesartan
138402-10-5

trityl irbesartan

A

methoxytriphenylmethane
596-31-6

methoxytriphenylmethane

B

2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-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
ConditionsYield
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%
methanol
67-56-1

methanol

trityl irbesartan
138402-10-5

trityl irbesartan

A

methoxytriphenylmethane
596-31-6

methoxytriphenylmethane

B

2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-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
ConditionsYield
for 10h; Heating / reflux;A 73%
B 71%
trityl irbesartan
138402-10-5

trityl irbesartan

2-n-butyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one hydrobromide
329055-24-5

2-n-butyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In ethanol; water at 20℃; for 3h;
trityl irbesartan
138402-10-5

trityl irbesartan

A

triphenylmethyl alcohol
76-84-6

triphenylmethyl alcohol

B

2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-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
ConditionsYield
With hydrogenchloride; water In acetone
trityl irbesartan
138402-10-5

trityl irbesartan

2-n-butyl-4-spirocyclopentane-1-[((2'-tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one hydrochloride
329055-23-4

2-n-butyl-4-spirocyclopentane-1-[((2'-tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one hydrochloride

Conditions
ConditionsYield
Stage #1: trityl irbesartan With methanol; potassium hydroxide for 2.5h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 20℃; for 4h; pH=0.99; Product distribution / selectivity;
Stage #1: trityl irbesartan With methanol; toluene-4-sulfonic acid In thioguanin for 24h; Heating / reflux;
Stage #2: With sodium hydroxide In water pH=12.7;
Stage #3: With hydrogenchloride; sodium hydroxide Product distribution / selectivity; more than 3 stages;
With hydrogenchloride In ethanol; water at 20℃; for 3h; Product distribution / selectivity;

138402-10-5Relevant articles and documents

Synthesis of amido-N-imidazolium salts and their applications as ligands in suzuki-miyaura reactions: Coupling of hetero- aromatic halides and the synthesis of milrinone and irbesartan

Kumar, Manian Rajesh,Park, Kyungho,Lee, Sunwoo

scheme or table, p. 3255 - 3266 (2011/02/23)

A new catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki-Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki-Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to give the corresponding aryl compounds in high yield. The yield was increased with increasing steric bulkiness of the substituted group. Especially, 1-(2,6-diisopropylphenyl)-3-N-(2,4,6-tri-tert- butylphenylacetamido)imidazolium bromide (4bc) exhibited 850,000 TON in the coupling reaction of 2-bromopyridine and phenylboronic acid. In addition, pharmaceutical compounds such as milrinone and irbesartan were synthesized via Suzuki-Miyaura coupling using sterically bulky, amido-N-imidazolium salt (4bc) as a ligand. Copyright

PROCESS FOR THE PREPARATION OF IRBESARTAN AND INTERMEDIATE PRODUCTS

-

Page/Page column 13, (2010/01/07)

The present invention relates to a new method for the production of irbesartan, having the chemical name 2-n-butyl-4-spirocyclopentane-1-[(2'-(tetrazol-5-yl)biphenyl-4-yl)methyl]-2- imidazolin-5-one, and pharmacologically acceptable salts thereof. Furthermore the invention relates to new (intermediate) compounds which are suitable for the production of irbesartan.

Process for the preparation of 2-alkyl-1-((2'-substituted-biphenyl-4-yl) Methyl)-imidazole, dihydroimidazole or benzimidazloe derivatives

-

Page/Page column 6, (2009/07/18)

The invention relates to a new process for the preparation of sartans 2-butyl-3-[[2′-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1′-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one is disclosed, which proceeds via novel intermediate, 4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenylboronic acid (Formula (II)) or its analogs. Compound (II) reacts with 5-(2-bromophenyl)-1-(triphenylmethyl)-1H-tetrazole (III) in the presence of catalyst, using conditions of Suzuki reaction, to give trityl irbesartan (I), whereas analogs to compound (II) may give candesartan, valsartan, telmisartan, losartan and olmesartan.

PROCESSES FOR THE SYNTHESIS OF 5-PHENYL -1 TRITYL-1H-TETRAZOLE

-

Page/Page column 17, (2010/11/30)

Provided are processes for the synthesis of 5 -phenyl- 1-trityl-lH-tetrazole, an intermediate useful in the synthesis of irbesartan.

Synthesis and screening for acetylcholinesterase inhibitor activity of some novel 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-ones: Derivatives of irbesartan key intermediate

Kavitha,Gaonkar,Narendra Sharath Chandra,Sadashiva,Rangappa

, p. 7391 - 7398 (2008/09/17)

The association of bioactive nucleus with other pharmacological agents is hoped to improve the efficacy of the treatment by combining the effects of different pharmacological mechanisms of action. Keeping this in view, a series of 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-one derivatives have been synthesized by interaction of 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-one with different bioactive aralkyl halides in presence of powdered potassium carbonate by two different methods viz., conventional and microwave irradiation. The yields under conventional and microwave irradiation methods were in the range of 60-65% and 80-90%, respectively. The structure elucidation of the new compounds has been carried out with the help of elemental analysis and spectral data. All the synthesized compounds have been screened for their efficacy as acetylcholinesterase (AChE) inhibitor. AChE inhibitory activity study was carried out by using Ellman colorimetric assay with neostigmine as a reference standard against targets from different species, such as pure electric eel AChE, human serum AChE, and rat brain AChE. Among the compounds synthesized, compounds 5a, 5b, 5j showed good inhibition against AChE.

Process for preparation of Irbesartan

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Page/Page column 13-14, (2008/06/13)

A process for the preparation of Irbesartan of formula (I) using the steps of: (i) reacting 4′ aminomethyl-2-cyano biphenyl of formula (VI) with 1-veleramido cyclopentane carboxylic acid of formula (V) ?in an organic solvent and in the presence of an acid, without activating the —COOH group of compound of formula (V) to give 1-(2′cyanobiphenyl-4-yl-methylaminocarbonyl)-1-pentanoylamino cyclopentane of formula (VII). ?converting the compound of formula (VII) obtained in step (i) to Irbesartan of formula (I) by reacting the compound of the formula (VII) with tributyl tin azide in o-xylene to give Irbesartan of formula (I).

AN IMPROVED PROCESS FOR PREPARATION OF IRBESARTAN

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Page/Page column 23-24, (2008/06/13)

A process for the preparation of Irbesartan of formula (I): Formula (I) comprising the steps of: (i) reacting 4' aminomethyl-2-cyano biphenyl of formula (VI) with 1-veleramido cyclopentane carboxylic acid of formula (V): Formula (VI) and Formula (V) in an organic solvent and in the presence of an acid, without activating the -COOH group of compound of formula (V) to give 1-(2'cyanobiphenyl-4-yl-methylaminocarbonyl)-1-pentanoylamino cyclopentane of formula (VII). Formula (VII) converting the compound of formula (VII) obtained in step (i) to Irbesartan of formula (I) by reacting the compound of the formula (VII) with tributyl tin azide in o-xylene to give Irbesartan of formula (I).

PREPARATION OF TETRAZOLE DERIVATIVE

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Page/Page column 10-11, (2008/06/13)

The present invention relates to a process for the preparation of irbesartan or its pharmaceutically acceptable salts comprising a synthesis of trityl irbesartan by a reaction of 5-(4-(bromomethyl)biphenyl-2-yl)-1-(triphenylmethyl)tetrazole and 2-n-butyl-4-cyclopentane-2-imidazolin-5-one or a salt therof in an organic solvent in the presence of a phase transfer catalyst and a base, a removal of the protecting group and an isolation of irbesartan or its pharmaceutically acceptable salt.

PROCESSES FOR THE PREPARATION OF HIGHLY PURE IRBESARTAN

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Page/Page column 9; 10, (2010/02/11)

The present invention relates to processes for synthesis of highly pure irbesartan or pharmaceutically acceptable salts thereof.

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