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Synthetic route

: 114772-55-3
2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With sodium azide In 1-methyl-pyrrolidin-2-one	99%
With sodium azide In toluene at 20℃;	95%
With sodium azide; zinc trifluoromethanesulfonate In water at 100℃; for 6h; Solvent; Temperature; Time; Green chemistry;	91%

: 67-56-1
methanol

: 124751-00-4
2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

A: 596-31-6
methoxytriphenylmethane

B: 114798-26-4
lorsartan

Conditions

Conditions	Yield
for 7h; Heating / reflux;	A 90% B 98%

...Expand

: 1-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen at 20℃; under 760.051 Torr; for 24h;	97%
With palladium on carbon; hydrogen; acetic acid at 20℃; for 12h;	94%
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol; toluene / 0.5 h / 25 °C / Inert atmosphere 2: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 8 h / 25 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / toluene / 0.58 h / 0 - 25 °C 2: 5% palladium on barium sulphate; ammonium formate / water; isopropyl alcohol / 8 h / 60 °C View Scheme

: 124751-00-4
2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

A: 596-31-6
methoxytriphenylmethane

B: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol 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 - 4.2;	A n/a B 95%
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol With hydrogenchloride In methanol; water; acetone at 20℃; for 2h; Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=3.8 - 4.2;	A n/a B 93%
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol With sulfuric acid In methanol; water; acetone at 20℃; for 2h; Stage #2: With sodium hydroxide In methanol; water; acetone at 20 - 25℃; pH=3.8 - 4.2;	A n/a B 91.3%

: 141-78-6
ethyl acetate

A: C24H25ClN6O2

B: 596-31-6
methoxytriphenylmethane

C: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol 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 - 4.2; Stage #3: ethyl acetate at 40℃; for 1h;	A n/a B n/a C 95%

...Expand

: 124751-00-4
2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol; hydroxylamine hydrochloride In methanol at 60℃; for 2.5h; pH=2.95; Stage #2: With triethylamine In methanol at 0 - 40℃; for 1h; pH=3.6; Product distribution / selectivity;	94.7%
Stage #1: 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol; hydroxyammonium sulfate In isopropyl alcohol at 60 - 65℃; for 4h; pH=2.4; Stage #2: With triethylamine In isopropyl alcohol at 0 - 5℃; for 2h; pH=3.5; Product distribution / selectivity;	93.8%
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 4h;	90%

: 2-n-butyl-4-chloro-5-hydroxymethyl-1-[[2'-(1H-tetrazole-5-yl)[1,1'-biphenyl]-4-yl]]-1H-imidazole sodium salt

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With sulfuric acid In water; ethyl acetate at 10 - 25℃; for 1h; pH=3.6 - 3.8; Purification / work up;	94%

: 124750-99-8
cozaar

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With sulfuric acid In water; ethyl acetate at 10 - 25℃; for 1h; pH=3.6 - 3.8; Purification / work up;	93%
With hydrogenchloride In tetrahydrofuran; water; chlorobenzene	86.8%
With hydrogenchloride In tetrahydrofuran; water; chlorobenzene pH=3.5 - 3.6;	84%
With hydrogenchloride In tetrahydrofuran; water; chlorobenzene pH=3.5 - 3.6;	42.6 g

: 2-n-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol p-toluenesulfonate

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 15 - 25℃; pH=3.5 - 3.6;	93%

: 133909-99-6
2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 25℃; for 4h;	89%

: trityl losartan

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With methanol for 4 - 5h; Heating / reflux;	88%

: (1-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-2-butyl-4-chloro-1H-imidazol-5-yl)methanol

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 25 - 60℃; for 8h;	71%
With 5% palladium on barium sulphate; ammonium formate In water; isopropyl alcohol at 60℃; for 8h; Temperature; Time;	70.7%

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

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With sodium tetrahydroborate; sodium hydroxide In water at 5 - 20℃; for 4.41667h;	65%
With sodium tetrahydroborate; water; sodium hydroxide In acetonitrile at 5 - 25℃; for 4.41667h;	29.2%
Stage #1: 2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde With sodium tetrahydroborate In water at 25 - 45℃; Stage #2: With hydrogenchloride In water at 15 - 20℃; pH=4.0;

: C30H33ClN6O2

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Stage #1: C30H33ClN6O2 With trifluoroacetic acid In methoxybenzene at 60℃; for 1.5h; Stage #2: With potassium hydroxide In water; methoxybenzene	49%

: 852357-69-8
(2-butyl-5-chloro-3-{2'-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Stage #1: (2-butyl-5-chloro-3-{2'-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol With water; hydrogen bromide at 15 - 20℃; for 4h; Stage #2: With sodium acetate In water Product distribution / selectivity;
Stage #1: (2-butyl-5-chloro-3-{2'-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol With hydrogenchloride In dichloromethane; water at 0 - 10℃; for 2h; Stage #2: With sodium acetate In dichloromethane; water Product distribution / selectivity;

: 57598-33-1
2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 4: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 6: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 7 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 4: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 5: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 6: sodium borohydride / CH2Cl2 / 24 h / 25 °C 7: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: tetrahydrofuran / 2 h / 20 °C
2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
3: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
4: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
6: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

Multi-step reaction with 7 steps
1: tetrahydrofuran / 2 h / 20 °C
2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
3: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h
4: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
5: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C
6: sodium borohydride / CH2Cl2 / 24 h / 25 °C
7: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

: 114772-53-1
2-Cyano-4'-methylbiphenyl

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 2: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 4: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 5 steps 1: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 2: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 4: sodium borohydride / CH2Cl2 / 24 h / 25 °C 5: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 80 °C / Green chemistry 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C / Green chemistry 3: sodium tetrahydroborate / methanol / 1.17 h / 20 - 40 °C / Green chemistry 4: sodium azide; zinc trifluoromethanesulfonate / water / 6 h / 100 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / tetrachloromethane 2: sodium methylate / N-methyl-acetamide; hexane; ethyl acetate; N,N-dimethyl-formamide 3: ammonium chloride / ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile View Scheme

: 79047-41-9
2-n-butyl-4-chloro-5-hydroxymethylimidazole

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 77 percent / 1.0 N aq. ceric ammonium nitrate / acetic acid / 3 h / 25 °C 2: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 3: sodium borohydride / CH2Cl2 / 24 h / 25 °C 4: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: NH4Ca(NO3)3; sodium hydroxide / acetic acid 2: sodium hydroxide; sodium tetrahydroborate / water; toluene 3: hydrogenchloride; sodium hydroxide; acetic acid / methanol; water; ethyl acetate; toluene View Scheme

: 83857-96-9
2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 2: sodium borohydride / CH2Cl2 / 24 h / 25 °C 3: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 20 h / 25 - 85 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol; toluene / 0.5 h / 25 °C / Inert atmosphere 3: ammonium formate; 5% palladium on barium sulphate / isopropyl alcohol; water / 8 h / 25 - 60 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C / Green chemistry 2: sodium tetrahydroborate / methanol / 1.17 h / 20 - 40 °C / Green chemistry 3: sodium azide; zinc trifluoromethanesulfonate / water / 6 h / 100 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl acetamide / 5 h / 20 °C 2.1: sodium tetrahydroborate / methanol; N,N-dimethyl acetamide / 1 h / 5 - 20 °C 3.1: sodium azide; triethylamine hydrochloride / N,N-dimethyl acetamide / 16 h / 120 °C 3.2: 80 °C / pH 4.0 View Scheme
Multi-step reaction with 3 steps 1: sodium carbonate; tetraethylammonium bromide / toluene / 90 - 95 °C 2: sodium tetrahydroborate; sodium hydroxide / water / 20 - 85 °C 3: sodium azide; triethylamine hydrochloride / toluene / 90 - 95 °C View Scheme

: 114772-54-2
4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 3: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C / Green chemistry 2: sodium tetrahydroborate / methanol / 1.17 h / 20 - 40 °C / Green chemistry 3: sodium azide; zinc trifluoromethanesulfonate / water / 6 h / 100 °C / Green chemistry View Scheme
Multi-step reaction with 2 steps 1: sodium methylate / N-methyl-acetamide; hexane; ethyl acetate; N,N-dimethyl-formamide 2: ammonium chloride / ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl acetamide / 5 h / 20 °C 2.1: sodium tetrahydroborate / methanol; N,N-dimethyl acetamide / 1 h / 5 - 20 °C 3.1: sodium azide; triethylamine hydrochloride / N,N-dimethyl acetamide / 16 h / 120 °C 3.2: 80 °C / pH 4.0 View Scheme
Multi-step reaction with 3 steps 1: sodium carbonate; tetraethylammonium bromide / toluene / 90 - 95 °C 2: sodium tetrahydroborate; sodium hydroxide / water / 20 - 85 °C 3: sodium azide; triethylamine hydrochloride / toluene / 90 - 95 °C View Scheme

: 74201-13-1
N-(2-hydroxy-1,1-dimethyl)-2-methoxybenzamide

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: thionyl chloride / 1 h / 25 °C 2: tetrahydrofuran / 2 h / 20 °C 3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 4: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 7: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 8 steps 1: thionyl chloride / 1 h / 25 °C 2: tetrahydrofuran / 2 h / 20 °C 3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 4: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 5: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 6: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 7: sodium borohydride / CH2Cl2 / 24 h / 25 °C 8: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: thionyl chloride / 1 h / 25 °C
2: tetrahydrofuran / 2 h / 20 °C
3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
4: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
7: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

Multi-step reaction with 8 steps
1: thionyl chloride / 1 h / 25 °C
2: tetrahydrofuran / 2 h / 20 °C
3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
4: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h
5: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
6: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C
7: sodium borohydride / CH2Cl2 / 24 h / 25 °C
8: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

: 84392-32-5
4,4-dimethyl-2-(4'-methyl-biphenyl-2-yl)-4,5-dihydrooxazole

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 5: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 6 steps 1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 2: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 3: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 4: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 5: sodium borohydride / CH2Cl2 / 24 h / 25 °C 6: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
5: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

Multi-step reaction with 6 steps
1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
2: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h
3: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
4: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C
5: sodium borohydride / CH2Cl2 / 24 h / 25 °C
6: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

: 133909-97-4
N-(trityl)-5-[4΄-(methyl)biphenyl-2-yl]-2H-tetrazole

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 2: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 3: sodium borohydride / CH2Cl2 / 24 h / 25 °C 4: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

: 133051-88-4
N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 2: sodium borohydride / CH2Cl2 / 24 h / 25 °C 3: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

: 133910-00-6
2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / CH2Cl2 / 24 h / 25 °C 2: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

: 579-75-9
2-Methoxybenzoic acid

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 95 percent / thionyl chloride / 18 h / 20 °C 2: CH2Cl2 / 2 h / 20 °C 3: thionyl chloride / 1 h / 25 °C 4: tetrahydrofuran / 2 h / 20 °C 5: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 6: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 7: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 9: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 10 steps 1: 95 percent / thionyl chloride / 18 h / 20 °C 2: CH2Cl2 / 2 h / 20 °C 3: thionyl chloride / 1 h / 25 °C 4: tetrahydrofuran / 2 h / 20 °C 5: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 6: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 7: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 8: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 9: sodium borohydride / CH2Cl2 / 24 h / 25 °C 10: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 95 percent / thionyl chloride / 18 h / 20 °C
2: CH2Cl2 / 2 h / 20 °C
3: thionyl chloride / 1 h / 25 °C
4: tetrahydrofuran / 2 h / 20 °C
5: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
6: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
7: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
9: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

Multi-step reaction with 10 steps
1: 95 percent / thionyl chloride / 18 h / 20 °C
2: CH2Cl2 / 2 h / 20 °C
3: thionyl chloride / 1 h / 25 °C
4: tetrahydrofuran / 2 h / 20 °C
5: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
6: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h
7: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
8: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C
9: sodium borohydride / CH2Cl2 / 24 h / 25 °C
10: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

: 21615-34-9
2-Methoxybenzoyl chloride

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: CH2Cl2 / 2 h / 20 °C 2: thionyl chloride / 1 h / 25 °C 3: tetrahydrofuran / 2 h / 20 °C 4: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 5: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 6: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 8: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme
Multi-step reaction with 9 steps 1: CH2Cl2 / 2 h / 20 °C 2: thionyl chloride / 1 h / 25 °C 3: tetrahydrofuran / 2 h / 20 °C 4: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 5: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 6: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 7: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 8: sodium borohydride / CH2Cl2 / 24 h / 25 °C 9: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: CH2Cl2 / 2 h / 20 °C
2: thionyl chloride / 1 h / 25 °C
3: tetrahydrofuran / 2 h / 20 °C
4: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
5: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
6: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h
8: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

Multi-step reaction with 9 steps
1: CH2Cl2 / 2 h / 20 °C
2: thionyl chloride / 1 h / 25 °C
3: tetrahydrofuran / 2 h / 20 °C
4: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C
5: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h
6: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating
7: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C
8: sodium borohydride / CH2Cl2 / 24 h / 25 °C
9: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C
View Scheme

: 2-n-butyl-4-chloro-5-hydroxymethyl-1-[[2'-(1H-tetrazole-5-yl)[1,1'-biphenyl]-4-yl]]-1H-imidazole magnesium salt

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With sulfuric acid In water; ethyl acetate at 10 - 25℃; for 1h; pH=3.6 - 3.8; Purification / work up;

: 2-n-butyl-4-chloro-5-hydroxymethyl-1-[[2'-(1H-tetrazole-5-yl)[1,1'-biphenyl]-4-yl]]-1H-imidazole calcium salt

: 114798-26-4
lorsartan

Conditions

Conditions	Yield
With sulfuric acid In water; ethyl acetate at 10 - 25℃; for 1h; pH=3.6 - 3.8; Purification / work up;

: 114798-26-4
lorsartan

: 79-11-8
chloroacetic acid

: chloroacetyl losartan

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In tetrahydrofuran at 0 - 20℃;	100%

: 76-83-5
trityl chloride

: 114798-26-4
lorsartan

: 124751-00-4
2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	98.5%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;	96%
With triethylamine In N,N-dimethyl-formamide at 20℃;

: 114798-26-4
lorsartan

: 124750-99-8
cozaar

Conditions

Conditions	Yield
With potassium tert-butylate In isopropyl alcohol at 10 - 25℃; Product distribution / selectivity;	94%
Stage #1: lorsartan With potassium hydroxide In isopropyl alcohol Stage #2: In cyclohexane at 20 - 50℃; for 3h;	93.7%
With potassium hydroxide In water; acetonitrile for 0.25 - 0.333333h; Product distribution / selectivity;	92%

: 114798-26-4
lorsartan

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

Conditions

Conditions	Yield
With dipyridinium dichromate In N,N-dimethyl-formamide at 20 - 50℃; for 6h; Alkaline conditions;	94%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 6h;	53%
With ruthenium trichloride; potassium metaperiodate; diperiodatocuprate(III) dihydrate; potassium nitrate; potassium hydroxide In water at 25℃; for 2h; Kinetics; Temperature; Sealed tube; Inert atmosphere;

: 114798-26-4
lorsartan

: losartan hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran	93.7%

: 114798-26-4
lorsartan

: 124750-99-8
losartan potassium

Conditions

Conditions	Yield
With potassium hydroxide In methanol; isopropyl alcohol at 20℃; for 0.5h;	90%
With potassium hydroxide In methanol for 4h; Heating / reflux;	33%
With potassium hydroxide In methanol for 1h; pH=9; Reflux;

: 114798-26-4
lorsartan

: 2-n-butyl-4-chloro-5-hydroxymethyl-1-[[2'-(1H-tetrazole-5-yl)[1,1'-biphenyl]-4-yl]]-1H-imidazole sodium salt

Conditions

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 38 - 40℃; for 0.5h; pH=10 - 12; Product distribution / selectivity;	87%
With sodium t-butanolate In isopropyl alcohol Product distribution / selectivity;
With sodium hydroxide In water at 20℃; pH=9.62; Product distribution / selectivity;

: 15761-38-3
L-N-Boc-Ala

: 114798-26-4
lorsartan

: 1174760-85-0
(S)-(1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methyl 2-(tert-butoxycarbonyl)aminopropanoate

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 24.5h;	79%

: 114798-26-4
lorsartan

: 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

Conditions	Yield
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;

: 114798-26-4
lorsartan

: 2-n-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In tetrahydrofuran	78%

: 114798-26-4
lorsartan

: 646511-09-3
3‐[(nitrooxy)methyl]benzoic acid

: 3-nitrooxymethyl-benzoic acid 2-butyl-5-chloro-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 2h;	72%

: 104-15-4
toluene-4-sulfonic acid

: 114798-26-4
lorsartan

: 2-n-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol p-toluenesulfonate

Conditions

Conditions	Yield
In tetrahydrofuran; chlorobenzene	71.5%

: 838878-70-9
pentafluorophenol 4-nitroxybutyrate

: 114798-26-4
lorsartan

: 838876-22-5
2-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-5-[(3-nitrooxypropyl)carbonyloxy]methyl-1H-imidazole

Conditions

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	53%

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