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139481-59-7 Usage

Uses

antihypertensive, angiotensin II inhibitor

Chemical Properties

Crystalline Solid

Uses

An angiotensin II type-1 receptor antagonist. Used in treatment of congestive heart failure. Antihypertensive

Brand name

Atacand (AstraZeneca).

Definition

ChEBI: A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin eceptor antagonist used for the treatment of hypertension.
InChI:InChI:1S/C24H20N6O3/c1-2-33-24-25-20-9-5-8-19(23(31)32)21(20)30(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-26-28-29-27-22/h3-13H,2,14H2,1H3,(H,31,32)(H,26,27,28,29)

139481-59-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1087870)  Candesartan cilexetil Related Compound G  United States Pharmacopeia (USP) Reference Standard 139481-59-7 1087870-10MG 14,500.98CNY Detail

139481-59-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Candesartan

1.2 Other means of identification

Product number -
Other names 1-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic acid

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:139481-59-7 SDS

139481-59-7Synthetic route

methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate
139481-69-9

methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Stage #1: methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate With sodium hydroxide; water In methanol at 78 - 80℃; for 1h;
Stage #2: With acetic acid In ethyl acetate at 10 - 15℃; pH=4 - 5;
95%
With methanol; sodium hydroxide; water at 10 - 70℃;90%
With sodium hydroxide In methanol at 80 - 90℃; for 1h;85%
ethyl 2-ethoxy-1-{[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl}-benzimidazole-7-carboxylate
856414-35-2

ethyl 2-ethoxy-1-{[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl}-benzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
With lithium hydroxide In ethanol at 80℃; for 3h;85%
ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate
139481-58-6

ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Stage #1: ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate With sodium hydroxide; ethanol; water for 24h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol; water pH=4 - 4.5;
80%
Stage #1: ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate With sodium hydroxide; water In o-xylene at 25 - 65℃; for 3h;
Stage #2: With acetic acid In methanol pH=4.5 - 5.5;
With water; sodium hydroxide at 40 - 80℃; Reagent/catalyst;
candesartan cilexetil

candesartan cilexetil

A

methanol-methyl carbonate

methanol-methyl carbonate

B

candesartan
139481-59-7

candesartan

C

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane at 30℃; for 8h;A n/a
B 78.01%
C n/a
methanol ethyl acetate
914771-42-9

methanol ethyl acetate

ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate
139481-58-6

ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
With sodium hydroxide In ethanol67%
methyl 2-carboxy-3-nitrobenzoate
21606-04-2

methyl 2-carboxy-3-nitrobenzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: SOCl2, DMF / toluene / 0.5 h / Heating
2: NaN3 / acetone; H2O / 1 h
3: 1.5 h / Heating
4: 85 percent / K2CO3 / acetonitrile / 4 h / Heating
5: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
6: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
7: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
8: 100 percent / trimethyltin azide / toluene / 29 h / Heating
9: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / toluene / 2.5 h / 75 °C
2.1: sodium azide; tetrabutylammomium bromide / toluene / 4 h / -10 - -5 °C
2.2: 1 h / 80 - 85 °C
3.1: potassium carbonate; tetrabutylammomium bromide / toluene / 12 h / 80 - 85 °C
3.2: 3 h / Reflux
4.1: tin(ll) chloride / ethyl acetate / 1.5 h / Reflux
4.2: 4.5 h / -10 - 0 °C
4.3: 0.5 h / Reflux
5.1: acetic acid / toluene / 6 h / Reflux
6.1: sodium azide; tributyltin chloride / toluene / 100 h / Reflux
6.2: 0 - 20 °C
7.1: sodium hydroxide; water / ethanol / 3.5 h / Reflux
7.2: 3 h / 0 °C / pH 4
View Scheme
acid chloride of 1-methylhydrogen-3-nitrophthalate
73833-13-3

acid chloride of 1-methylhydrogen-3-nitrophthalate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: NaN3 / acetone; H2O / 1 h
2: 1.5 h / Heating
3: 85 percent / K2CO3 / acetonitrile / 4 h / Heating
4: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
5: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
6: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
7: 100 percent / trimethyltin azide / toluene / 29 h / Heating
8: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium azide; tetrabutylammomium bromide / toluene / 4 h / -10 - -5 °C
1.2: 1 h / 80 - 85 °C
2.1: potassium carbonate; tetrabutylammomium bromide / toluene / 12 h / 80 - 85 °C
2.2: 3 h / Reflux
3.1: tin(ll) chloride / ethyl acetate / 1.5 h / Reflux
3.2: 4.5 h / -10 - 0 °C
3.3: 0.5 h / Reflux
4.1: acetic acid / toluene / 6 h / Reflux
5.1: sodium azide; tributyltin chloride / toluene / 100 h / Reflux
5.2: 0 - 20 °C
6.1: sodium hydroxide; water / ethanol / 3.5 h / Reflux
6.2: 3 h / 0 °C / pH 4
View Scheme
3-nitrophthalic acid
603-11-2

3-nitrophthalic acid

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: concd. H2SO4 / methanol
2: SOCl2, DMF / toluene / 0.5 h / Heating
3: NaN3 / acetone; H2O / 1 h
4: 1.5 h / Heating
5: 85 percent / K2CO3 / acetonitrile / 4 h / Heating
6: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
7: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
8: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
9: 100 percent / trimethyltin azide / toluene / 29 h / Heating
10: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: sulfuric acid / 24.75 h / 20 - 65 °C
2.1: N,N-dimethyl-formamide; thionyl chloride / toluene / 2.5 h / 75 °C
3.1: sodium azide; tetrabutylammomium bromide / toluene / 4 h / -10 - -5 °C
3.2: 1 h / 80 - 85 °C
4.1: potassium carbonate; tetrabutylammomium bromide / toluene / 12 h / 80 - 85 °C
4.2: 3 h / Reflux
5.1: tin(ll) chloride / ethyl acetate / 1.5 h / Reflux
5.2: 4.5 h / -10 - 0 °C
5.3: 0.5 h / Reflux
6.1: acetic acid / toluene / 6 h / Reflux
7.1: sodium azide; tributyltin chloride / toluene / 100 h / Reflux
7.2: 0 - 20 °C
8.1: sodium hydroxide; water / ethanol / 3.5 h / Reflux
8.2: 3 h / 0 °C / pH 4
View Scheme
methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate
57113-90-3

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating
2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
4: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
5: 100 percent / trimethyltin azide / toluene / 29 h / Heating
6: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; tetrabutylammomium bromide / toluene / 12 h / 80 - 85 °C
1.2: 3 h / Reflux
2.1: tin(ll) chloride / ethyl acetate / 1.5 h / Reflux
2.2: 4.5 h / -10 - 0 °C
2.3: 0.5 h / Reflux
3.1: acetic acid / toluene / 6 h / Reflux
4.1: sodium azide; tributyltin chloride / toluene / 100 h / Reflux
4.2: 0 - 20 °C
5.1: sodium hydroxide; water / ethanol / 3.5 h / Reflux
5.2: 3 h / 0 °C / pH 4
View Scheme
2-Azidocarbonyl-3-nitro-benzoic acid methyl ester
856414-36-3

2-Azidocarbonyl-3-nitro-benzoic acid methyl ester

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.5 h / Heating
2: 85 percent / K2CO3 / acetonitrile / 4 h / Heating
3: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
4: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
5: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
6: 100 percent / trimethyltin azide / toluene / 29 h / Heating
7: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate
136304-78-4

methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
2: 100 percent / trimethyltin azide / toluene / 29 h / Heating
3: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid / toluene / 6 h / Reflux
2.1: sodium azide; tributyltin chloride / toluene / 100 h / Reflux
2.2: 0 - 20 °C
3.1: sodium hydroxide; water / ethanol / 3.5 h / Reflux
3.2: 3 h / 0 °C / pH 4
View Scheme
methyl 2-<<2'-cyanobiphenyl-4-yl)methyl>amino>-3-nitrobenzoate
139481-28-0

methyl 2-<<2'-cyanobiphenyl-4-yl)methyl>amino>-3-nitrobenzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
2: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
3: 100 percent / trimethyltin azide / toluene / 29 h / Heating
4: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 4 steps
1.1: tin(ll) chloride / ethyl acetate / 1.5 h / Reflux
1.2: 4.5 h / -10 - 0 °C
1.3: 0.5 h / Reflux
2.1: acetic acid / toluene / 6 h / Reflux
3.1: sodium azide; tributyltin chloride / toluene / 100 h / Reflux
3.2: 0 - 20 °C
4.1: sodium hydroxide; water / ethanol / 3.5 h / Reflux
4.2: 3 h / 0 °C / pH 4
View Scheme
methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate
139481-44-0

methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / trimethyltin azide / toluene / 29 h / Heating
2: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
Multi-step reaction with 2 steps
1: azido tributyltin (IV) / N,N-dimethyl-formamide / 20 h / 140 - 150 °C
2: sodium hydroxide; water / 20 h / 70 - 80 °C
View Scheme
methyl 2-amino>-3-nitrobenzoate
139481-38-2

methyl 2-amino>-3-nitrobenzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature
2: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h
3: 91 percent / acetic acid / 0.67 h / 80 - 90 °C
4: 100 percent / trimethyltin azide / toluene / 29 h / Heating
5: 85 percent / 1 N aq. NaOH / methanol / 1 h / 80 - 90 °C
View Scheme
methyl 1-[(2-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate

methyl 1-[(2-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium azide; tributyltin chloride / toluene / 100 h / Reflux
1.2: 0 - 20 °C
2.1: sodium hydroxide; water / ethanol / 3.5 h / Reflux
2.2: 3 h / 0 °C / pH 4
View Scheme
candesartan cilexetil
145040-37-5

candesartan cilexetil

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
With Bis(p-nitrophenyl) phosphate In dimethyl sulfoxide; acetonitrile at 37℃; for 0.0333333h; pH=7.5; Reagent/catalyst; Enzymatic reaction;
methyl 2-ethoxy-1-<<2'-biphenyl-4-yl>methyl>-1H-benzimidazole-7-carboxylate

methyl 2-ethoxy-1-<<2'-biphenyl-4-yl>methyl>-1H-benzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
With methanol; sodium hydroxide at 50℃; for 3h;44.5 g
2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester
150058-27-8

2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium tert-butylate / N,N-dimethyl acetamide / 60 °C / Inert atmosphere
2: sodium hydroxide; methanol / 3 h / 50 °C
View Scheme
ethyl 1-[(2'-cyano-[1,1']-biphenyl-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
139481-41-7

ethyl 1-[(2'-cyano-[1,1']-biphenyl-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: azido tributyltin (IV) / 5,5-dimethyl-1,3-cyclohexadiene / 20 h / 140 - 150 °C
2: sodium hydroxide; water / 40 - 80 °C
View Scheme
ethyl 1-(4-bromobenzyl)-2-ethoxy-benzimidazole-7-carboxylate
854538-88-8

ethyl 1-(4-bromobenzyl)-2-ethoxy-benzimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / palladium diacetate; triphenylphosphine / water; toluene / 16 h / 60 - 70 °C
2.1: sodium hydroxide; ethanol; water / 24 h / Heating / reflux
2.2: pH 4 - 4.5
View Scheme
ethyl 3-amino-2-(4-bromobenzylamine)-benzoate
916891-90-2

ethyl 3-amino-2-(4-bromobenzylamine)-benzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid / 1 h / 80 °C
2.1: potassium carbonate / palladium diacetate; triphenylphosphine / water; toluene / 16 h / 60 - 70 °C
3.1: sodium hydroxide; ethanol; water / 24 h / Heating / reflux
3.2: pH 4 - 4.5
View Scheme
ethyl 2-(4-bromobenzylamine)-3-nitrobenzoate
854538-89-9

ethyl 2-(4-bromobenzylamine)-3-nitrobenzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tin(ll) chloride / ethanol / 2 h / Heating / reflux
1.2: 0 °C
2.1: sodium hydroxide; water
3.1: acetic acid / 1 h / 80 °C
4.1: potassium carbonate / palladium diacetate; triphenylphosphine / water; toluene / 16 h / 60 - 70 °C
5.1: sodium hydroxide; ethanol; water / 24 h / Heating / reflux
5.2: pH 4 - 4.5
View Scheme
ethyl 3-amino-2-(4-bromobenzylamine)-benzoate hydrochloride

ethyl 3-amino-2-(4-bromobenzylamine)-benzoate hydrochloride

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide; water
2.1: acetic acid / 1 h / 80 °C
3.1: potassium carbonate / palladium diacetate; triphenylphosphine / water; toluene / 16 h / 60 - 70 °C
4.1: sodium hydroxide; ethanol; water / 24 h / Heating / reflux
4.2: pH 4 - 4.5
View Scheme
ethyl 2-ethoxy-1-[[2'-[(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-[1,1']biphenyl-4-yl]methyl]-1H-benzoimidazole-7-carboxylate
916891-91-3

ethyl 2-ethoxy-1-[[2'-[(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-[1,1']biphenyl-4-yl]methyl]-1H-benzoimidazole-7-carboxylate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium formate / palladium 10% on activated carbon / ethanol / 72 h / Heating / reflux
2.1: sodium hydroxide; ethanol; water / 24 h / Heating / reflux
2.2: pH 4 - 4.5
View Scheme
ethyl 2-chloro-3-nitrobenzoate
3979-45-1

ethyl 2-chloro-3-nitrobenzoate

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / toluene / 12 h / Heating / reflux
2.1: tin(ll) chloride / ethanol / 2 h / Heating / reflux
2.2: 0 °C
3.1: sodium hydroxide; water
4.1: acetic acid / 1 h / 80 °C
5.1: potassium carbonate / palladium diacetate; triphenylphosphine / water; toluene / 16 h / 60 - 70 °C
6.1: sodium hydroxide; ethanol; water / 24 h / Heating / reflux
6.2: pH 4 - 4.5
View Scheme
2-chloro-3-nitrobezoic acid
3970-35-2

2-chloro-3-nitrobezoic acid

candesartan
139481-59-7

candesartan

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sulfuric acid / 24 h / 15 - 30 °C / Heating / reflux
2.1: triethylamine / toluene / 12 h / Heating / reflux
3.1: tin(ll) chloride / ethanol / 2 h / Heating / reflux
3.2: 0 °C
4.1: sodium hydroxide; water
5.1: acetic acid / 1 h / 80 °C
6.1: potassium carbonate / palladium diacetate; triphenylphosphine / water; toluene / 16 h / 60 - 70 °C
7.1: sodium hydroxide; ethanol; water / 24 h / Heating / reflux
7.2: pH 4 - 4.5
View Scheme
candesartan
139481-59-7

candesartan

(1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazol-7-yl)methanol
924654-25-1

(1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazol-7-yl)methanol

Conditions
ConditionsYield
Stage #1: candesartan With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 50℃; for 6.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
96.5%
With lithium aluminium tetrahydride In tetrahydrofuran at -78℃;90%
Stage #1: candesartan With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;
Stage #2: With water In tetrahydrofuran at 0℃; for 0.5h;
77%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;77%
trityl chloride
76-83-5

trityl chloride

candesartan
139481-59-7

candesartan

2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid
139481-72-4

2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 15 - 23℃; for 3.5h; Temperature; Flow reactor; Large scale;94%
With triethylamine In acetone at 55 - 60℃; for 4 - 8h; Product distribution / selectivity;90%
With triethylamine In acetone at 55 - 60℃; Product distribution / selectivity;90%
candesartan
139481-59-7

candesartan

C24H20N6O3*H3N

C24H20N6O3*H3N

Conditions
ConditionsYield
With ammonium hydroxide In water for 2h;89%
ethylenediamine
107-15-3

ethylenediamine

candesartan
139481-59-7

candesartan

C24H20N6O3*C2H8N2

C24H20N6O3*C2H8N2

Conditions
ConditionsYield
In water for 2h;85%
Trimethylenediamine
109-76-2

Trimethylenediamine

candesartan
139481-59-7

candesartan

C24H20N6O3*C3H10N2

C24H20N6O3*C3H10N2

Conditions
ConditionsYield
In water for 2h;80%
trityl chloride
76-83-5

trityl chloride

candesartan
139481-59-7

candesartan

2-ethoxy-1-<<2'-biphenyl-4-yl>methyl>-1H-benzimidazole-7-carboxylic acid
894806-43-0

2-ethoxy-1-<<2'-biphenyl-4-yl>methyl>-1H-benzimidazole-7-carboxylic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h; Ambient temperature;76%
zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

candesartan
139481-59-7

candesartan

C24H18N6O3(2-)*2C3H7NO*Zn(2+)

C24H18N6O3(2-)*2C3H7NO*Zn(2+)

Conditions
ConditionsYield
In methanol68%
ethyl acetate-benzene

ethyl acetate-benzene

trityl chloride
76-83-5

trityl chloride

candesartan
139481-59-7

candesartan

2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid
139481-72-4

2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane66%
pyridine
110-86-1

pyridine

water
7732-18-5

water

candesartan
139481-59-7

candesartan

cadmium(II) iodide

cadmium(II) iodide

C24H18N6O3(2-)*Cd(2+)*C5H5N*H2O

C24H18N6O3(2-)*Cd(2+)*C5H5N*H2O

Conditions
ConditionsYield
In methanol at 150℃; for 72h; Autoclave;56%
4,4'-bipyridine
553-26-4

4,4'-bipyridine

zinc(II) sulfate heptahydrate

zinc(II) sulfate heptahydrate

candesartan
139481-59-7

candesartan

2C24H18N6O3(2-)*2Zn(2+)*C10H8N2

2C24H18N6O3(2-)*2Zn(2+)*C10H8N2

Conditions
ConditionsYield
In methanol; water at 135℃; for 72h; Autoclave;45%
1-chloromethyl-3-methylbutylamine hydrochloride
1160386-36-6

1-chloromethyl-3-methylbutylamine hydrochloride

candesartan
139481-59-7

candesartan

2-Ethoxy-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid (1-chloromethyl-3-methylbutyl)amide
1160386-25-3

2-Ethoxy-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid (1-chloromethyl-3-methylbutyl)amide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DCM at 20℃;15%
candesartan
139481-59-7

candesartan

uridine-5'-diphospho-α-D-glucuronic acid trisodium salt
63700-19-6

uridine-5'-diphospho-α-D-glucuronic acid trisodium salt

candesartan-O-glucuronide

candesartan-O-glucuronide

Conditions
ConditionsYield
With saccharic acid-1,4-lactone; recombinant human UDP-glucuronyltransferase 1A8 at 37℃; for 48h;7.4%
candesartan
139481-59-7

candesartan

uridine-5'-diphospho-α-D-glucuronic acid trisodium salt
63700-19-6

uridine-5'-diphospho-α-D-glucuronic acid trisodium salt

candesartan-N2-glucuronide

candesartan-N2-glucuronide

Conditions
ConditionsYield
With saccharic acid-1,4-lactone; recombinant human UDP-glucuronyltransferase 1A3 at 37℃; for 48h;4%
candesartan
139481-59-7

candesartan

2-Ethoxy-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid acetoxymethyl ester

2-Ethoxy-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid acetoxymethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
2: potassium iodide, potassium carbonate / dimethylformamide / 2 h / 60 °C
3: 1N aq. HCl / methanol / 1.5 h / Ambient temperature
View Scheme
candesartan
139481-59-7

candesartan

2-Ethoxy-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid 1-acetoxy-ethyl ester

2-Ethoxy-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid 1-acetoxy-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
2: potassium iodide, potassium carbonate / dimethylformamide / 2 h / 60 °C
3: 1N aq. HCl / methanol / 1.5 h / Ambient temperature
View Scheme

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