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144689-93-0

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  • High Quality 99% 1H-Imidazole-5-carboxylicacid, 4-(1-hydroxy-1-methylethyl)-2-propyl-, ethyl ester 144689-93-0 ISO Manufacturer

    Cas No: 144689-93-0

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144689-93-0 Usage

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 144689-93-0 differently. You can refer to the following data:
1. An Olmesartan (O550000) intermediate.
2. Olmesartan (O550000) intermediate.

Check Digit Verification of cas no

The CAS Registry Mumber 144689-93-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,4,6,8 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 144689-93:
(8*1)+(7*4)+(6*4)+(5*6)+(4*8)+(3*9)+(2*9)+(1*3)=170
170 % 10 = 0
So 144689-93-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H20N2O3/c1-5-7-8-13-9(11(15)17-6-2)10(14-8)12(3,4)16/h16H,5-7H2,1-4H3,(H,13,14)

144689-93-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate

1.2 Other means of identification

Product number -
Other names 4-(1-Hydroxy-1-methylethyl)-2-propyl

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:144689-93-0 SDS

144689-93-0Synthetic route

methyl bromide
74-83-9

methyl bromide

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate
144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With iodine; magnesium In dichloromethane at 15 - 25℃; for 2h;97.5%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate
144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
In diethyl ether; dichloromethane at 10 - 15℃; for 1h;95%
ethanol
64-17-5

ethanol

C10H14N2O2
849206-42-4

C10H14N2O2

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: ethanol; C10H14N2O2 With sulfuric acid at 40 - 50℃;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;
92%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate
144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride; diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran at -10 - 0℃; for 0.166667h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; dichloromethane
85%
Stage #1: methylmagnesium chloride; diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran; toluene for 6.5h; Inert atmosphere; Cooling with ice;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene pH=7;
In tetrahydrofuran at 60℃; for 2h;4.81 g
4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid
144690-04-0

4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid

ethanol
64-17-5

ethanol

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: 4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid; ethanol With thionyl chloride Reflux;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;
85%
methylene chloride
74-87-3

methylene chloride

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate
144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: methylene chloride With magnesium In tetrahydrofuran for 0.5h; Reflux;
Stage #2: diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran at 30℃; for 2.5h; Solvent; Temperature;
80%
Stage #1: methylene chloride With magnesium at 55 - 60℃; for 1h; Inert atmosphere;
Stage #2: diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate at 0℃; for 8h;
2-propyl-1H-imidazole-4,5-dicarboxylic acid
58954-23-7

2-propyl-1H-imidazole-4,5-dicarboxylic acid

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / HCl / Ambient temperature
2: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C
View Scheme
2-propylimidazole-4,5-dicarbonitrile
51802-42-7

2-propylimidazole-4,5-dicarbonitrile

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / 6N aq. HCl / 8 h / Heating
2: 86 percent / HCl / Ambient temperature
3: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C
View Scheme
2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate
144689-94-1

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate

A

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

B

ethyl 2-butyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate
144689-92-9

ethyl 2-butyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate

Conditions
ConditionsYield
With methylmagnesium bromide In tetrahydrofuran
diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate hydrochloride

diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate hydrochloride

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; sodium chloride / water / 1 h / Cooling with ice
2.1: toluene; tetrahydrofuran / 6.5 h / Inert atmosphere; Cooling with ice
2.2: pH 7
View Scheme
4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid
144690-04-0

4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide / acetone / 48 h / 20 °C
2: sodium hydroxide; water / acetone / Reflux
3: thionyl chloride / Reflux
View Scheme
C10H14N2O2
849206-42-4

C10H14N2O2

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; water / acetone / Reflux
2: thionyl chloride / Reflux
View Scheme
5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole

5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

trityl olmesartan medoxomil
144690-92-6

trityl olmesartan medoxomil

Conditions
ConditionsYield
Stage #1: 5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole; ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate With tert-butylamine hydrobromide; potassium carbonate In acetone at 0 - 55℃; for 32h;
Stage #2: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one With potassium carbonate; potassium iodide In acetone at 20 - 55℃; for 3h;
98.5%
5-(2',3',5',6'-tetra-[2H]-4'-(bromomethyl)biphenyl-2-yl)-1-trityl-1H-tetrazole
1330277-14-9

5-(2',3',5',6'-tetra-[2H]-4'-(bromomethyl)biphenyl-2-yl)-1-trityl-1H-tetrazole

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2',3',5',6'-tetra-[2H]-2'-(1-trithyl-1H-terazol-5-yl)-biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate
1420880-39-2

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2',3',5',6'-tetra-[2H]-2'-(1-trithyl-1H-terazol-5-yl)-biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate With potassium tert-butylate In N,N-dimethyl-formamide for 0.333333h; Cooling with ice;
Stage #2: 5-(2',3',5',6'-tetra-[2H]-4'-(bromomethyl)biphenyl-2-yl)-1-trityl-1H-tetrazole In N,N-dimethyl-formamide at 20℃; for 2.5h;
96.5%
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carbohydrazide

4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carbohydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 16h; Reflux;95.3%
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid
144690-04-0

4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate With water; sodium hydroxide In acetone for 3h; Reflux;
Stage #2: With hydrogenchloride In water at 10℃; pH=6.5;
95%
With sodium hydroxide In water; acetone at 110℃; for 3h;82%
N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole
124750-51-2

N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate
144690-33-5

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole; ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate With potassium carbonate In butanone at 60℃; for 2h;
Stage #2: With N,N-dimethyl acetamide In butanone at 45℃; for 4h;
93.8%
With tetrabutylammomium bromide; potassium carbonate In acetone at 50 - 60℃; for 20h; Green chemistry;90.7%
With potassium carbonate In acetonitrile for 7h; Heating / reflux;89%
N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole
124750-51-2

N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

A

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate
144690-33-5

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({2'-[1-(triphenylmethyl)-1H-1,2,3,4-tetrazol-5-yl]-[1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylate

B

4-(1-hydroxy-1-methylethyl)-2-propyl-1-(4-(2-(1-(triphenylmethyl)tetrazol-5-yl)phenyl)phenyl)methylimidazole-5-carboxylic acid
761404-85-7

4-(1-hydroxy-1-methylethyl)-2-propyl-1-(4-(2-(1-(triphenylmethyl)tetrazol-5-yl)phenyl)phenyl)methylimidazole-5-carboxylic acid

C

C45H42N6O2

C45H42N6O2

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl acetamide at 60 - 65℃; for 6h; Solvent; Reagent/catalyst;A 89.6%
B 0.02%
C 0.02%
1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

3-(4-bromobenzyl)-5-(1-hydroxy-1-methylethyl)-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester
685091-51-4

3-(4-bromobenzyl)-5-(1-hydroxy-1-methylethyl)-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 20℃; for 18h; Product distribution / selectivity;89%
With potassium carbonate In DMA at 20℃; for 18h; Product distribution / selectivity;89%
With potassium carbonate In N,N-dimethyl acetamide for 48h;47%
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1.16667h; Product distribution / selectivity;45%
Stage #1: ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: 1-bromomethyl-4-bromobenzene In N,N-dimethyl-formamide for 1h; Product distribution / selectivity;
45%
2'-<2-(triphenylmethyl)-1H-tetrazol-5-yl><1,1'-biphenyl>-4-methanol
135050-95-2

2'-<2-(triphenylmethyl)-1H-tetrazol-5-yl><1,1'-biphenyl>-4-methanol

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate
172875-59-1

ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 10℃; for 0.5h; Reagent/catalyst; Solvent; Cooling with ice;89%
1-benzyl-5-[4'-(bromomethyl)biphenyl-2-yl]-1H-tetrazole

1-benzyl-5-[4'-(bromomethyl)biphenyl-2-yl]-1H-tetrazole

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 1-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 1-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 25 - 84℃; for 18h;83%
With potassium carbonate In acetonitrile at 84℃; for 18h;83.2%
With tetrabutylammomium bromide; potassium carbonate In acetone at 0 - 45℃; for 20.25h;165 g
N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole
133051-88-4

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

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate
172875-59-1

ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24h;83%
With potassium tert-butylate 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h; Yield given. Multistep reaction;
Stage #1: ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole In N,N-dimethyl-formamide at 20 - 60℃; for 6h;
N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole
124750-51-2

N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate
172875-59-1

ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate With potassium carbonate; tetrabutylammomium bromide In acetone at 20℃; for 1h;
Stage #2: N-(triephenylmethyl)-5-<4'-(bromomethyl)-biphenyl-2-yl>tetrazole In acetone for 14h; Heating / reflux;
80%
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

4-bromomethylphenylboronic acid pinacol ester
138500-85-3

4-bromomethylphenylboronic acid pinacol ester

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1H-imidazole-5-carboxylate

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; Sealed tube;64.9%
5-[4'-(chloromethyl)biphenyl-2-yl]-1-(2,4-dimethoxybenzyl)-1Htetrazole

5-[4'-(chloromethyl)biphenyl-2-yl]-1-(2,4-dimethoxybenzyl)-1Htetrazole

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 1-({2'-[1-(2,4-dimethoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 1-({2'-[1-(2,4-dimethoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In acetone at 0 - 65℃; for 89h;50%
4'-bromomethyl-biphenyl-2-carboxylic acid tert-butyl ester
114772-40-6

4'-bromomethyl-biphenyl-2-carboxylic acid tert-butyl ester

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate
144689-20-3

ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

Conditions
ConditionsYield
With potassium tert-butylate 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h; Yield given. Multistep reaction;
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 4-isopropenyl-2-propylimidazole-5-carboxylate
157356-73-5

ethyl 4-isopropenyl-2-propylimidazole-5-carboxylate

Conditions
ConditionsYield
With pyridine; trichlorophosphate 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h; Yield given. Multistep reaction;
1-(2-trimethylsilylethoxymethyl)-5-(4'-bromomethylbiphenyl-2-yl)-1H-tetrazole
1004758-90-0

1-(2-trimethylsilylethoxymethyl)-5-(4'-bromomethylbiphenyl-2-yl)-1H-tetrazole

2-(2-trimethylsilylethoxy)methyl-5-(4'-bromomethylbiphenyl-2-yl)-2H-tetrazole
1004758-92-2

2-(2-trimethylsilylethoxy)methyl-5-(4'-bromomethylbiphenyl-2-yl)-2H-tetrazole

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

A

ethyl 5-(1-hydroxy-1-methylethyl)-2-propyl-3-[[4-[2-(2-(2-trimethylsilylethoxymethyl)-2H-tetrazol-5-yl)phenyl]phenyl]methyl]-3H-imidazole-4-carboxylate

ethyl 5-(1-hydroxy-1-methylethyl)-2-propyl-3-[[4-[2-(2-(2-trimethylsilylethoxymethyl)-2H-tetrazol-5-yl)phenyl]phenyl]methyl]-3H-imidazole-4-carboxylate

B

ethyl 5-(1-hydroxy-1-methylethyl)-2-propyl-3-[[4-[2-(1-(2-trimethylsilylethoxymethyl)-1H-tetrazol-5-yl)phenyl]phenyl]methyl]-3H-imidazole-4-carboxylate

ethyl 5-(1-hydroxy-1-methylethyl)-2-propyl-3-[[4-[2-(1-(2-trimethylsilylethoxymethyl)-1H-tetrazol-5-yl)phenyl]phenyl]methyl]-3H-imidazole-4-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

ethyl 4-isopropyl-2-propylimidazole-5-carboxylate
172875-51-3

ethyl 4-isopropyl-2-propylimidazole-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h
2: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature
View Scheme
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropyl-2-propyl-3H-imidazole-4-carboxylic acid

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropyl-2-propyl-3H-imidazole-4-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h
2: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature
3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
4: 82 percent / HCl / dioxane / 16 h / Ambient temperature
5: 100 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature
View Scheme
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropenyl-2-propyl-3H-imidazole-4-carboxylic acid

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropenyl-2-propyl-3H-imidazole-4-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h
2: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
3: 92 percent / HCl / dioxane / 16 h / Ambient temperature
4: 94 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature
View Scheme
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester
172875-76-2

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h
2: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature
3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
4: 82 percent / HCl / dioxane / 16 h / Ambient temperature
View Scheme
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropenyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester
172875-80-8

3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropenyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h
2: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
3: 92 percent / HCl / dioxane / 16 h / Ambient temperature
View Scheme
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

1-[(2'-carboxybiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid

1-[(2'-carboxybiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
2: 92 percent / HCl / dioxane / 16 h / Ambient temperature
3: 91 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature
View Scheme
ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate
144689-93-0

ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate

XF 818

XF 818

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h
2: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature
3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h
4: 93 percent / 25percent aq. AcOH / 2.5 h / 80 °C
5: 89 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature
View Scheme

144689-93-0Downstream Products

144689-93-0Relevant articles and documents

Synthetic method for preparing olmesartan medoxomil intermediate through continuous flow

-

Paragraph 0036-0044, (2021/09/04)

The invention discloses a synthetic method for preparing an olmesartan medoxomil intermediate through continuous flow, which belongs to the technical field of drug synthesis. The method comprises the following steps: step (1), dissolving a compound 2-propyl-4,5-imidazole dicarboxylic acid ethyl ester I in an organic solvent to form a reaction phase A; step (2), taking a commercially purchased methyl magnesium chloride solution as a reaction phase B; step (3), pumping the reaction phase A and the reaction phase B into a mixer by using a plunger pump at a certain flow rate, then feeding the mixture into a reactor, retaining for a certain time, quenching by using an acid water phase C, feeding the mixture into an oil-water continuous liquid separator, separating liquid to obtain an organic solution of a compound as shown in a formula II, desolventizing, and recrystallizing to obtain the compound as shown in the formula II. The technical problems of low purity and high cost in the existing preparation process are solved, the product is high in purity and few in impurities, the content of the key impurity A, the key impurity B and the key impurity C can be controlled to be 0.1% or below, the raw materials are cheap and easy to obtain, the reaction condition is mild, operation is easy and convenient, the synthesis efficiency is high, and the method is suitable for industrial production. A novel continuous flow path is provided for preparing the olmesartan medoxomil and the intermediate.

4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-carboxylic ethyl ester monohydrate

-

Paragraph 0084; 0085; 0086; 0087, (2019/01/14)

The invention relates to a 4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-carboxylic ethyl ester monohydrate (namely a compound shown in a formula 2) and a preparation method and application thereof. The compound can be obtained by crystallization in organic solvents, such as an acetone and water mixed solvent, in mutual solubility with water. The 4-(1-hydroxyl-1-methylethyl)-2-propylimidazole-5-carboxylic ethyl ester monohydrate is high in purity and yield, and subsequent olmesartan medoxomil synthesis is benefited.

Amazingel medoxomill intermediate 4 - (1-hydroxy-1-methyl ethyl) - 2-propyl-imidazol-5-carboxylic acid ethyl ester preparation method and application

-

Paragraph 0070-0072, (2017/05/12)

The invention provides a preparation method of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazolyl-5-carboxylate (1). The method accurately controls the reaction material ratio, solvent composition, solvent consumption, reaction temperature, reaction time and other technological parameters, and obviously lowers the content of the impurity compound disclosed as Formula 3, thereby obtaining the high-purity olmesartan medoxomil. The invention also provides application of the compound disclosed as Formula 3 as a quality control standard substance in preparing the ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazolyl-5-carboxylate (1).

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