Candesartan supplier | CasNO.139481-59-7

Name
Candesartan
EINECS 604-138-8
CAS No. 139481-59-7
Article Data19
CAS DataBase
Density 1.41 g/cm³
Solubility Soluble in ethyl acetate, methanol, water (<1 mg/ml at 25°C), DMSO (88 mg/ml at 25°C), and ethanol (1 mg/ml at 25°C).
Melting Point 183-185 °C
Formula C₂₄H₂₀N₆O₃
Boiling Point 754.8 °C at 760 mmHg
Molecular Weight 440.461
Flash Point 410.3 °C
Transport Information
Appearance crystalline solid
Safety 26-36
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms Blopress (TN);Candesartan [USAN:INN];Blopress;CV 11974;2-Ethoxy-1-(p-(o-1H-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylic acid;Candesartan (USAN);1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-((2-(1H-tetrazol-5-yl)(1,1-biphenyl)-4-yl)methyl)-;Cyclohexyl-1-Chloro Ethyl Carbamate;
PSA 118.81000
LogP 4.02860

Synthetic route

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

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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%

: 856414-35-2
ethyl 2-ethoxy-1-{[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl}-benzimidazole-7-carboxylate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
With lithium hydroxide In ethanol at 80℃; for 3h;	85%

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

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

A: methanol-methyl carbonate

B: 139481-59-7
candesartan

C: 108-93-0
cyclohexanol

Conditions

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane at 30℃; for 8h;	A n/a B 78.01% C n/a

...Expand

: 914771-42-9
methanol ethyl acetate

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

: 139481-59-7
candesartan

Conditions

Conditions	Yield
With sodium hydroxide In ethanol	67%

: 21606-04-2
methyl 2-carboxy-3-nitrobenzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 73833-13-3
acid chloride of 1-methylhydrogen-3-nitrophthalate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 603-11-2
3-nitrophthalic acid

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 57113-90-3
methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 856414-36-3
2-Azidocarbonyl-3-nitro-benzoic acid methyl ester

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 136304-78-4
methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 139481-28-0
methyl 2-<<2'-cyanobiphenyl-4-yl)methyl>amino>-3-nitrobenzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 139481-44-0
methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 139481-38-2
methyl 2-amino>-3-nitrobenzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 145040-37-5
candesartan cilexetil

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 139481-59-7
candesartan

Conditions

Conditions	Yield
With methanol; sodium hydroxide at 50℃; for 3h;	44.5 g

: 150058-27-8
2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 139481-41-7
ethyl 1-[(2'-cyano-[1,1']-biphenyl-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 854538-88-8
ethyl 1-(4-bromobenzyl)-2-ethoxy-benzimidazole-7-carboxylate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 916891-90-2
ethyl 3-amino-2-(4-bromobenzylamine)-benzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 854538-89-9
ethyl 2-(4-bromobenzylamine)-3-nitrobenzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 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

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

: 3979-45-1
ethyl 2-chloro-3-nitrobenzoate

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 3970-35-2
2-chloro-3-nitrobezoic acid

: 139481-59-7
candesartan

Conditions

Conditions	Yield
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

Yield

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

: 139481-59-7
candesartan

: 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

Conditions	Yield
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%

: 76-83-5
trityl chloride

: 139481-59-7
candesartan

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

Conditions

Conditions	Yield
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%

: 139481-59-7
candesartan

: C24H20N6O3*H3N

Conditions

Conditions	Yield
With ammonium hydroxide In water for 2h;	89%

: 107-15-3
ethylenediamine

: 139481-59-7
candesartan

: C24H20N6O3*C2H8N2

Conditions

Conditions	Yield
In water for 2h;	85%

: 109-76-2
Trimethylenediamine

: 139481-59-7
candesartan

: C24H20N6O3*C3H10N2

Conditions

Conditions	Yield
In water for 2h;	80%

: 76-83-5
trityl chloride

: 139481-59-7
candesartan

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 1h; Ambient temperature;	76%

: 5970-45-6
zinc(II) acetate dihydrate

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

: 139481-59-7
candesartan

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

Conditions

Conditions	Yield
In methanol	68%

...Expand

ethyl acetate-benzene: ethyl acetate-benzene

: 76-83-5
trityl chloride

: 139481-59-7
candesartan

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane	66%

...Expand

: 110-86-1
pyridine

: 7732-18-5
water

: 139481-59-7
candesartan

: cadmium(II) iodide

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

Conditions

Conditions	Yield
In methanol at 150℃; for 72h; Autoclave;	56%

...Expand

: 553-26-4
4,4'-bipyridine

: zinc(II) sulfate heptahydrate

: 139481-59-7
candesartan

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

Conditions

Conditions	Yield
In methanol; water at 135℃; for 72h; Autoclave;	45%

...Expand

: 1160386-36-6
1-chloromethyl-3-methylbutylamine hydrochloride

: 139481-59-7
candesartan

: 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

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DCM at 20℃;	15%

: 139481-59-7
candesartan

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

: candesartan-O-glucuronide

Conditions

Conditions	Yield
With saccharic acid-1,4-lactone; recombinant human UDP-glucuronyltransferase 1A8 at 37℃; for 48h;	7.4%

: 139481-59-7
candesartan

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

: candesartan-N2-glucuronide

Conditions

Conditions	Yield
With saccharic acid-1,4-lactone; recombinant human UDP-glucuronyltransferase 1A3 at 37℃; for 48h;	4%

: 139481-59-7
candesartan

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

Conditions

Conditions	Yield
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

: 139481-59-7
candesartan

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

Conditions

Conditions	Yield
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 Specification

The Candesartan, with the CAS registry number 139481-59-7, is also known as 2-Ethoxy-3-[[4-[2-(1H-tetrazol-5-yl)phenyl]phenyl]methyl]-3H-benzoimidazole-4-carboxylic acid. It belongs to the product categories of Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Candesartan Cilexatil;Aromatics;Heterocycles.This chemical's molecular formula is C₂₄H₂₀N₆O₃ and molecular weight is 440.45. What's more,Its systematic name is 1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-.

Physical properties about Candesartan are: (1)ACD/LogP: 4.652; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.41; (4)ACD/LogD (pH 7.4): 0.54; (5)ACD/BCF (pH 5.5): 1.16; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 4.64; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 9; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.719; (13)Molar Refractivity: 122.545 cm3 ; (14)Molar Volume: 310.519 cm3; (15)Surface Tension: 59.6440010070801 dyne/cm; (16)Density: 1.418 g/cm3; (17)Flash Point: 410.262 °C; (18)Enthalpy of Vaporization: 115.396 kJ/mol; (19)Boiling Point: 754.756 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

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

The Candesartan is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin .In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)c1cccc2nc(OCC)n(c12)Cc5ccc(c3ccccc3c4nnnn4)cc5;
(2)Std. 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);
(3)Std. InChIKey:HTQMVQVXFRQIKW-UHFFFAOYSA-N;

Product Name

Candesartan

Synthetic route

Candesartan Specification

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