Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
- Product Name
- Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
- CAS No.
- 139481-44-0
- Chemical Name
- Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
- Synonyms
- 1-[(2´Azilsartan-19;Methyl 1-[(2´Azilsartan Impurity S;Azilsartan Impurity 31;Azilsartan Impurity 21;Azilsartan Impurity 27;Azilsartan Impurity 76;Azilsartan interMediate;Azilsartan interMediate B
- CBNumber
- CB51009654
- Molecular Formula
- C25H21N3O3
- Formula Weight
- 411.45
- MOL File
- 139481-44-0.mol
Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate Property
- Melting point:
- 168 °C
- storage temp.
- 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly, Sonicated)
- form
- Solid
- color
- Off-White to Light Yellow
- InChI
- InChI=1S/C25H21N3O3/c1-3-31-25-27-22-10-6-9-21(24(29)30-2)23(22)28(25)16-17-11-13-18(14-12-17)20-8-5-4-7-19(20)15-26/h4-14H,3,16H2,1-2H3
- InChIKey
- KSXLHOFDCDKQLH-UHFFFAOYSA-N
- SMILES
- C1(OCC)N(CC2=CC=C(C3=CC=CC=C3C#N)C=C2)C2=C(C(OC)=O)C=CC=C2N=1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H312Harmful in contact with skin
H315Causes skin irritation
H319Causes serious eye irritation
H332Harmful if inhaled
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P321Specific treatment (see … on this label).
P322Specific measures (see …on this label).
P330Rinse mouth.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
P363Wash contaminated clothing before reuse.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- M3197
- Product name
- Methyl 1-[(2'-Cyano-[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
- Packaging
- 25G
- Price
- $67
- Updated
- 2025/07/31
- Product number
- M3197
- Product name
- Methyl 1-[(2'-Cyano-[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
- Packaging
- 100G
- Price
- $204
- Updated
- 2025/07/31
- Product number
- C988330
- Product name
- 1-[(2''-Cyano-1,1''-biphenyl-4-yl)methyl]-2-ethoxy-7-benzimidazolecarboxylicAcidMethylEster
- Packaging
- 100g
- Price
- $595
- Updated
- 2021/12/16
- Product number
- 090880
- Product name
- Methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
- Purity
- 95+%
- Packaging
- 250mg
- Price
- $439
- Updated
- 2021/12/16
- Product number
- CHM0077727
- Product name
- 1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID, 1-[(2'-CYANO[1,1'-BIPHENYL]-4-YL)METHYL]-2-ETHOXY-METHYL ESTER
- Purity
- 95.00%
- Packaging
- 10MG
- Price
- $779.63
- Updated
- 2021/12/16
Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate Chemical Properties,Usage,Production
Description
Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate is a key synthetic intermediate in the synthesis of azilsartan, an angiotensin II.1 (AT1) receptor antagonist used in the treatment of hypertension.
Chemical Properties
Pale Yellow Solid
Uses
Intermediate in the synthesis of angiotensin II receptor antagonist.
Synthesis
78-09-1
136304-78-4
139481-44-0
Using methyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoate (MBA) and tetraethyl orthocarbonate (TEC, 397 kg) as the raw material, the mixture was heated at reflux in the presence of acetic acid (62 kg) at 78 to 82 °C for 1 to 2 hours. After completion of the reaction, the reaction solution was cooled and methanol (1680 L), 24% aqueous sodium hydroxide (65 L) and water (2030 L) were added sequentially. The mixture was stirred at 60 to 30 °C for 2 h and the pH was adjusted with aqueous sodium hydroxide solution to 5 to 7. After cooling to below 5 °C, the precipitated crystals were separated and washed with cold water (2500 L) and cold ethyl acetate (500 L) to obtain the first batch of crystals. The mother liquor and washings were concentrated under reduced pressure, cooled to below 5 °C, and the precipitated crystals were separated and washed with cold ethyl acetate (20 L) to obtain the second batch of crystals. The first and second batches of crystals were combined, dissolved in ethyl acetate (4890 L) and heated to reflux. The crystal seeds were added at about 70 °C and then cooled to 5 °C. The crystals were separated, washed with cold ethyl acetate (200 L) and dried to give methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (BEC, 361 kg, 84.8% yield). The product melting point was 168.5-169.5 °C. 1H-NMR (200 MHz, CDCl3) δ: 1.42 (3H, t), 3.71 (3H, s), 4.63 (2H, q), 5.59 (2H, s), 7.09 (2H, d), 7.20 (1H, t), 7.45-7.59 (5H, m), 7.69- 7.80 (2H, m), 7.92 (1H, dd).IR (KBr) cm-1: 2225, 1725, 1550, 1480, 1430, 1280, 1250, 1040, 760, 750.
References
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: EP1420016, 2004, A1. Location in patent: Page 18-19
[3] Patent: WO2009/157001, 2009, A2. Location in patent: Page/Page column 3
Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate Preparation Products And Raw materials
Raw materials
Preparation Products
Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate Suppliers
- Tel
- 0576-85016990 15014006640
- 1002779550@qq.com
- Country
- China
- ProdList
- 161
- Advantage
- 58
- Tel
- 0571-63811159 18906514933
- sales@dahaibiochem.com
- Country
- China
- ProdList
- 499
- Advantage
- 58
- Tel
- 18210857532; 18210857532
- Fax
- 86-10-82849933
- jkinfo@jkchemical.com
- Country
- China
- ProdList
- 96815
- Advantage
- 76
- Tel
- 021-021-58432009 400-005-6266
- Fax
- 021-58436166
- sales8178@energy-chemical.com
- Country
- China
- ProdList
- 44801
- Advantage
- 61
- Tel
- 13817811078
- Fax
- 86-021-50426522,50426273
- sales@jingyan-chemical.com
- Country
- China
- ProdList
- 9976
- Advantage
- 60
- Tel
- 0573-85285100 18627885956
- Fax
- 0573-85285100
- isenchem@163.com
- Country
- China
- ProdList
- 9310
- Advantage
- 66
- Tel
- 400-6009262 16621234537
- Fax
- 021-64823266
- chenyj@titansci.com
- Country
- China
- ProdList
- 14101
- Advantage
- 59
- Tel
- 025-83697070
- Fax
- +86-25-83453306
- info@chemlin.com.cn
- Country
- China
- ProdList
- 15883
- Advantage
- 64
- Tel
- 021-54306202 13764082696
- info@hanhongsci.com
- Country
- China
- ProdList
- 42934
- Advantage
- 64
- Tel
- 021-50135380
- shchemsky@sina.com
- Country
- China
- ProdList
- 32321
- Advantage
- 50
View Lastest Price from Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate manufacturers
- Product
- Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate 139481-44-0
- Price
- US $1.00/g
- Min. Order
- 100g
- Purity
- 99
- Supply Ability
- 1000
- Release date
- 2025-08-11
- Product
- Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate 139481-44-0
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-11-26
- Product
- Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate 139481-44-0
- Price
- US $220.00/KG
- Min. Order
- 100g
- Purity
- 99%
- Supply Ability
- 1T
- Release date
- 2021-06-02