Product Name

Synthetic route

2-butyl-4-chloro-1-[2'-(1H-tetrazol-5-yl) 1,1'-biphenyl-methyl]imidazole-5-carboxylic acid ethyl ester
947330-97-4

2-butyl-4-chloro-1-[2'-(1H-tetrazol-5-yl) 1,1'-biphenyl-methyl]imidazole-5-carboxylic acid ethyl ester

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 90℃; for 20h;90%
cozaar
124750-99-8

cozaar

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: cozaar With potassium permanganate In water at -5 - 50℃; for 16h;
Stage #2: With hydrogenchloride In water pH=2 - 3;		89.1%
Stage #1: cozaar With potassium hydroxide In water at 2℃; for 2h;
Stage #2: With sodium periodate; ruthenium trichloride In water; isopropyl alcohol at 4 - 20℃; for 22h;
Stage #3: With phosphoric acid In water; isopropyl alcohol for 0.5h;
Stage #1: cozaar With ruthenium trichloride; potassium hydroxide; sodium periodate In water at 0℃;
Stage #2: With phosphoric acid In water; isopropyl alcohol at 30℃; for 0.5h;
lorsartan
114798-26-4

lorsartan

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
With pyridine; potassium permanganate; tetrabutyl-ammonium chloride In water; acetone at 40 - 50℃; for 1h; Product distribution / selectivity;78%
With sodium periodate; ruthenium(III) trichloride hydrate; potassium hydroxide In water at 0℃;
Stage #1: lorsartan With sodium periodate; ruthenium (III) chloride monohydrate; potassium hydroxide In water at 0℃;
Stage #2: In water; isopropyl alcohol at 25℃; for 2.5h;
Stage #3: With phosphoric acid In water; isopropyl alcohol at 30℃; for 0.5h;
With cytochrome P450 2C9 Enzymatic reaction;
With cytochrome b5; NADPH In aq. phosphate buffer at 37℃; for 0.75h; Kinetics; Reagent/catalyst; Enzymatic reaction;
losartan potassium
124750-99-8

losartan potassium

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: losartan potassium With pyridine; potassium permanganate; tetrabutyl-ammonium chloride In water; acetone at 40 - 50℃; for 1h;
Stage #2: With hydrogenchloride In water; acetone Product distribution / selectivity;		72%
Stage #1: losartan potassium With potassium hydroxide In water at 2℃; for 2h;
Stage #2: With sodium periodate; ruthenium trichloride In water at 4 - 6.5℃; for 19h;
cozaar
124750-99-8

cozaar

A

2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde
114798-36-6

2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde

B

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
With manganese(IV) oxide In water at 80 - 180℃; for 0.833333h; microwave irradiation;A 0.253 mmol
B 64%
With manganese(IV) oxide In water at 80 - 180℃; for 0.25h; microwave irradiation;A 60%
B n/a
2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde
114798-36-6

2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
With potassium permanganate; potassium hydroxide In water; N,N-dimethyl-formamide at 20 - 30℃; for 2h; Large scale;
2-n-butyl-5-chloro-3H-imidazole-4-carboxylic acid ethyl ester

2-n-butyl-5-chloro-3H-imidazole-4-carboxylic acid ethyl ester

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrabutylammomium bromide; sodium hydroxide / toluene / 20 h / 60 °C
2: sodium azide; trimethylamine hydrochloride / toluene; 1-methyl-pyrrolidin-2-one / 43 h / 60 °C
3: sodium hydroxide / ethanol / 20 h / 90 °C
View Scheme
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile
114772-54-2

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid
124750-92-1

2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrabutylammomium bromide; sodium hydroxide / toluene / 20 h / 60 °C
2: sodium azide; trimethylamine hydrochloride / toluene; 1-methyl-pyrrolidin-2-one / 43 h / 60 °C
3: sodium hydroxide / ethanol / 20 h / 90 °C
View Scheme

Losartan carboxylic acid Specification

The CAS register number of Losartan carboxylic acid is 124750-92-1. It also can be called as 2-Butyl-4-chloro-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]imidazole-5-carboxylic acid and the IUPAC name about this chemical is 2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylic acid. The molecular formula about this chemical is C22H21ClN6O2 and molecular weight is 436.89. It belongs to the following product categories, such as Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals and so on. This chemical can be used as a metabolite of Losartan.

Physical properties about Losartan carboxylic acid are: (1)ACD/LogP: 3.61; (2)ACD/LogD (pH 5.5): -0.1; (3)ACD/LogD (pH 7.4): -0.53; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 8; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 8; (11)Polar Surface Area: 87.72Å2; (12)Index of Refraction: 1.695; (13)Molar Refractivity: 119.08 cm3; (14)Molar Volume: 309.7 cm3; (15)Polarizability: 47.21x10-24cm3; (16)Surface Tension: 56.7 dyne/cm; (17)Enthalpy of Vaporization: 108.7 kJ/mol; (18)Boiling Point: 707.8 °C at 760 mmHg; (19)Vapour Pressure: 5.04E-21 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1c(Cl)nc(n1Cc4ccc(c2ccccc2c3nnnn3)cc4)CCCC
(2)InChI: InChI=1/C22H21ClN6O2/c1-2-3-8-18-24-20(23)19(22(30)31)29(18)13-14-9-11-15(12-10-14)16-6-4-5-7-17(16)21-25-27-28-26-21/h4-7,9-12H,2-3,8,13H2,1H3,(H,30,31)(H,25,26,27,28)
(3)InChIKey: ZEUXAIYYDDCIRX-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C22H21ClN6O2/c1-2-3-8-18-24-20(23)19(22(30)31)29(18)13-14-9-11-15(12-10-14)16-6-4-5-7-17(16)21-25-27-28-26-21/h4-7,9-12H,2-3,8,13H2,1H3,(H,30,31)(H,25,26,27,28)
(5)Std. InChIKey: ZEUXAIYYDDCIRX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 441mg/kg (441mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 3959, 1994.

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