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Telmisartan

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Name

Telmisartan

EINECS 620-494-7
CAS No. 144701-48-4 Density 1.24 g/cm3
PSA 72.94000 LogP 7.26440
Solubility insoluble in water Melting Point 261-263 °C
Formula C33H30N4O2 Boiling Point 771.9 °C at 760 mmHg
Molecular Weight 514.627 Flash Point 420.6 °C
Transport Information N/A Appearance White or off white crystalline powder
Safety 22-24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 144701-48-4 (Telmisartan) Hazard Symbols IrritantXi
Synonyms

(1,1-Biphenyl)-2-carboxylic acid, 4-((1,4-dimethyl-2-propyl(2,6-bi-1H-benzimidazol)-1-yl)methyl)-;Micardis;4-((4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic acid;Timetazidine;4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]- [1,1'-biphenyl]-2-carboxylic acid;

Article Data 56

Telmisartan Synthetic route

144702-27-2

4'-[[2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-1H-benzimidazol-1-yl]-methyl]-2-cyano-biphenyl

144701-48-4

telmisatran

Conditions
ConditionsYield
Stage #1: 4'-[[2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-1H-benzimidazol-1-yl]-methyl]-2-cyano-biphenyl With sodium hydroxide; water In ethylene glycol for 8h; Heating / reflux;
Stage #2: With acetic acid In water; ethylene glycol at 20℃; pH=4; Product distribution / selectivity;
98%
Stage #1: 4'-[[2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-1H-benzimidazol-1-yl]-methyl]-2-cyano-biphenyl With potassium hydroxide; water In ethylene glycol at 140 - 150℃; for 21h;
Stage #2: With hydrogenchloride In water; ethylene glycol at 20℃; pH=7; Product distribution / selectivity;
98%
Stage #1: 4'-[[2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-1H-benzimidazol-1-yl]-methyl]-2-cyano-biphenyl With water; potassium hydroxide In ethylene glycol at 150 - 155℃;
Stage #2: With water; acetic acid for 2h; pH=4 - 4.5; Product distribution / selectivity;
98.7%
528560-93-2

4'-[[4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic acid methyl ester

144701-48-4

telmisatran

Conditions
ConditionsYield
Stage #1: 4'-[[4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic acid methyl ester With methanol; sodium hydroxide; water for 2h; Heating / reflux;
Stage #2: With acetic acid In water
98.6%
Stage #1: 4'-[[4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic acid methyl ester With methanol; potassium hydroxide for 24h; Reflux;
Stage #2: With formic acid Product distribution / selectivity;
96%
Stage #1: 4'-[[4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic acid methyl ester With sodium hydroxide In methanol; water for 3h; Reflux;
Stage #2: With acetic acid In methanol; water pH=5;
95%
152628-02-9

2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole

150766-86-2

4'-bromomethylbiphenyl-2-carboxylic acid

144701-48-4

telmisatran

Conditions
ConditionsYield
Stage #1: 2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole With sodium hydride In N,N-dimethyl-formamide at 0 - 5℃; for 1h;
Stage #2: 4'-bromomethylbiphenyl-2-carboxylic acid In N,N-dimethyl-formamide at 10℃; Solvent; Reagent/catalyst; Temperature;
95%
515815-48-2

tert-butyl-4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate hydrochloride

144701-48-4

telmisatran

Conditions
ConditionsYield
Stage #1: tert-butyl-4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate hydrochloride With acetic acid In water Heating / reflux;
Stage #2: With sodium hydroxide In water at 80 - 90℃;
93.3%
With sodium hydroxide; water In water; acetic acid at 80 - 90℃; Heating / reflux;93.3%
144702-26-1

tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate

144701-48-4

telmisatran

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 100℃; Reagent/catalyst; Solvent;93%
With trifluoroacetic acid In N,N-dimethyl-formamide for 4h;70%
With trifluoroacetic acid In N-methyl-acetamide63.9%
With trifluoroacetic acid In dichloromethane for 24h; Ambient temperature; Yield given;
960356-44-9

4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylic acid ammonium salt

144701-48-4

telmisatran

Conditions
ConditionsYield
Stage #1: 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylic acid ammonium salt With pyrographite In methanol at 25℃; for 0.5h;
Stage #2: With acetic acid In methanol at 5℃; for 1h;
93%
at 60℃; for 12h; Temperature; Time;91%

4'-[(2-butyrylamino-3-methyl-5-(1N-methyl-1H-benzimidazol-2-yl)-phenylamino)-methyl]-biphenyl-2-carboxylic acid isopropyl ester

144701-48-4

telmisatran

Conditions
ConditionsYield
Stage #1: 4'-[(2-butyrylamino-3-methyl-5-(1N-methyl-1H-benzimidazol-2-yl)-phenylamino)-methyl]-biphenyl-2-carboxylic acid isopropyl ester With acetic acid for 3h; Reflux;
Stage #2: With sodium hydroxide In ethanol for 12h; Reflux;
Stage #3: With hydrogenchloride In ethanol; water for 1h; pH=5 - 6; Cooling;
92%
172525-90-5

4'-[(2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-benzimidazol-1-yl)methyl]-biphenyl-2-carboxaldehyde

144701-48-4

telmisatran

Conditions
ConditionsYield
With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10 - 20℃; for 1.5h;90.6%
With oxone In N,N-dimethyl acetamide at 20 - 120℃; for 27.5h;
With sodium perborate In acetic acid at 100℃;

C25H25BN2O4

49572-60-3

2-bromo-1-methyl-1H-benzo[d]imidazole

144701-48-4

telmisatran

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate In 1,4-dioxane at 80℃; for 6h; Reagent/catalyst; Solvent; Suzuki Coupling; Inert atmosphere;90.05%
915124-86-6

4’-((1,7′-dimethyl-2′-propyl-1H,3′H-[2,5′-bibenzo[d]imidazol]-3′-yl)methyl)-[1,1′-biphenyl]-2-carboxamide

144701-48-4

telmisatran

Conditions
ConditionsYield
Stage #1: 4’-((1,7′-dimethyl-2′-propyl-1H,3′H-[2,5′-bibenzo[d]imidazol]-3′-yl)methyl)-[1,1′-biphenyl]-2-carboxamide With sulfuric acid In water at 125℃; for 28h;
Stage #2: With sodium hydroxide In dichloromethane; water pH=5.4;
89%
Stage #1: 4’-((1,7′-dimethyl-2′-propyl-1H,3′H-[2,5′-bibenzo[d]imidazol]-3′-yl)methyl)-[1,1′-biphenyl]-2-carboxamide With potassium hydroxide In propylene glycol at 85 - 150℃;
Stage #2: With water; acetic acid at 25 - 85℃; for 1.25h;
84%

Telmisartan Consensus Reports

It is believed that telmisartan’s dual mode of action may provide protective benefits against the vascular and renal damage caused by diabetes and cardiovascular disease (CVD).

Telmisartan Specification

1. Introduction of Telmisartan

Telmisartan, with the IUPAC Name of 2-[4-[[4-Methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]methyl]phenyl]benzoic acid
Synonyms of Telmisartan (CAS NO.144701-48-4): 4'[(1,4'-Dimethyl-2'-propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl][1,1'-biphenyl]-2-carboxylic acid, is one kind of white or off white crystalline powder. This chemical belongs to the Product Categories which include Pharmaceutical material and intermeidates; Active Pharmaceutical Ingredients; INTERMEDIATESOF; Antihypertensive; Imidazoles; (intermediates of telmisartan); Telmisartan;Hypertension; Intermediates & Fine Chemicals; Pharmaceuticals; API's. Telmisartan is also an angiotensin II receptor antagonist used in the management of hypertension.

2. Properties of Telmisartan

Telmisartan has the following properties: (1)Index of Refraction: 1.667; (2)Molar Refractivity: 154.51 cm3; (3)Molar Volume: 414.9 cm3; (4)Surface Tension: 48.7 dyne/cm; (5)Density: 1.24 g/cm3; (6)Flash Point: 420.6 °C; (7)Enthalpy of Vaporization: 117.87 kJ/mol; (8)Boiling Point: 771.9 °C at 760 mmHg; (9)Vapour Pressure: 4.58E-25 mmHg at 25°C; (10)Melting Point: 261-263°C; (11)Solubility: DMSO: >5 mg/mL at 60 °C; (12)Water Solubility: insoluble.

3. Safety Information of Telmisartan

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26 
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 2

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