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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
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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
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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..…

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N-Bromosuccinimide Price

TCI Chemical
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
TCI Chemical
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
TRC
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
American Custom Chemicals Corporation
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
AK Scientific
Product number
W3051
Product name
Methyl 1-[(2'-Cyano-[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
Packaging
500g
Price
$860
Updated
2021/12/16
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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

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

Americas 1 Canada 1 China 311 Europe 1 India 16 Japan 1 United Kingdom 2 United States 13 Global 346
TCI Chemicals (India) Pvt. Ltd.
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CHEMSWORTH
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View Lastest Price from Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate manufacturers

Handan City Zechi trading Co., LTD
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
Hebei Zhuanglai Chemical Trading Co Ltd
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
Baoji Guokang Healthchem Co., Ltd.
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

139481-44-0, Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylateRelated Search:

Tribenuron methyl Methyl 4-cyanobenzoate Kresoxim-methyl Methyl carbamate Benzimidazole Methyl salicylate Methyl benzoate Methylparaben Ethyl-2-Ethoxy-1-[[(2'-Cyanobiphenyl-4-yl) Methyl] Benzimidazole]-7-Carboxylate Methyl anthranilate Methyl formate METSULFURON METHYL Candesartan Candesartan cilexetil Trityl candesartan Ethyl -2-ethoxy-1-[[(2-(1Htetrazol-5-yl)biphenyl-4-yl-) methyl] Thiophanate-methyl Methyl

  • 1H-BENZIMIDAZOLE-7-CARBOXYLICACID, 1-[(2'-CYANO[1,1'-BIPHENYL]-4-YL)METHYL]-2-ETHOXY-METHYLESTER
  • 1-(2-cyanobiphenyl-4-yl-methyl)- 2-ethoxybenzimidazole-7-carboxylic acid ethyl ester
  • Azilsartan Impurity 31
  • 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-, methyl ester
  • Azilsartan-19
  • Azilsartan impurity 20/Methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
  • methyl 1-((2'-cyano-[1,1'-biphenyl]
  • Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
  • 1-[(2'-Cyano-1,1'-biphenyl-4-yl)Methyl]-2-ethoxy-7-benziMidazolecarboxylic Acid Methyl Ester
  • 3-[(2'-Cyanobiphenyl-4-yl)Methyl]-2-ethoxy-3H-benziMidazole-4-carboxylic Acid Methyl Ester
  • Methyl 1-[(2'-Cyanobiphenyl-4-yl)Methyl]-2-ethoxybenziMidazole-7-carbo
  • Methyl 1-((2'-cyanobiphenyl-4-yl)Methyl)-2-ethoxy-1H-benzo[d]iMidazole-7-carboxylate
  • IH-BENZIMIDAZOLE-7-CARBOXXYLIC ACID,1-((2'-CYANO(1,1-BIPHENYL)-4-YL)METHYL)-2-ETHOXY-ETHYL ESTER
  • Methyl1-[(2'-cyanobiphenyl-4-yl)Methyl]-2-ethoxy-benziMidazole-7-carboxylate
  • MeEthyl-2-ethoxy-1-[[(2'-cyanobiphenyl-4-yl)Methyl]benziMidazole]-7 -carboxylate
  • Azilsartan MedoxoMil InterMediate
  • Azilsartan interMediate
  • Methyl1-[(2'-cyanobiphenyl-4-yl)Methyl]-2-ethoxy-1H-benziMidazole-7-carboxylat
  • Azilsartan interMediate B
  • 1-[(2'-Cyanobiphenyl-4-yl)Methyl]-2-ethoxy-1H-benzo[d]iMidazole-7-carboxylic acid Methyl ester
  • 3-[[4-(2-cyanophenyl)phenyl]methyl]-2-ethoxy-4-benzimidazolecarboxylic acid methyl ester
  • -cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
  • Candesartan ester intermediate (methyl C6)
  • Azilsartan Impurity 21
  • Azilsartan Impurity 27
  • Azilsartan Impurity S
  • METHYL 1-(2'-CYANOBIPHENYL-4-YL)METHYL-2-ETHOXY BENZIMIDAZOLE-7-CARBOXYLATE(EBC-II)
  • Candesartan (C6) methyl ester intermediates
  • Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate(C6 methylester)
  • Azilsartan Nitrile Methyl Ester
  • Methyl 1-[(2'-Cyanobiphenyl-4-yl) Methyl]-2-Ethoxy-1H-enzimidazole-7-Carboxylate
  • 1-[(2'-Cyano-[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic Acid Methyl Ester
  • CANDESARTAN INTERMEDIATE(METHYL ESTER C6)
  • Azilsartan & Candesartan Cilexetil intermediates
  • Methyl1-[(2’cynobiphenyl-4-yl)\methyl]-2-ethoxybenzimidazole-7-carboxylate
  • Methyl1-[(2'cynobiphenyl-4-yl)\methyl]-2-ethoxybenzimidazole-7-carboxylatedine-3-carboxylate
  • Azilsartan Impurity 76
  • 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
  • Methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2- ethoxy-1ethyl)-2-H-benzo[d]imidazole-7-carboxylate
  • ethyl 3-((2'-carbamoyl-[1,1'-biphenyl]-4-yl)methyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate
  • Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-Ethoxy-1H-Benzimidazole-7-Carboxylate [CDS-7]
  • Methyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
  • Methyl 1-(2'-cyanobiphenyl-4-yl)methyl-2-ethoxy-1H-benzodimidazol-7-carboxylate
  • Methyl 2-ethoxy-1-[(2'-cyanobiphenyl-4-yl)-methyl]-1Hbenzimidazole-7-carboxylate
  • Methyl 3-((2'-cyanobiphenyl-4-yl) methyl)-2-ethoxy-3H-benzo [d]imidazole-4-carboxylate
  • Methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
  • Azilsartan Impurity 1 methyl 1-((2'-cyano-[1,1'-biphenyl]-4-yl)methyl) -2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
  • 1-[(2’-Cyano-1,1’-biphenyl-4-yl)methyl]-2-ethoxy-7-benzimidazolecarboxylic Acid Methyl Ester
  • 1-[(2'-Cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylicacidmethylester
  • 1-[(2′-Cyano-1,1′-biphenyl-4-yl)methyl]-2-ethoxy-7-benzimidazolecarboxylic acid methyl ester, CAS 139481-44-0
  • 1-[(2&acute
  • -cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
  • Methyl 1-[(2&acute
  • (Z)-Methyl-2-ethoxy-1-((2'-(N'-hydroxycarbamimidoyl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7- carboxylate (Intermediate of Azilsartan)
  • 139481-44-0
  • 1883681-10-1
  • Aromatics
  • Heterocycles