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| | (Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate Basic information |
| Product Name: | (Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate | | Synonyms: | (Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate;(Z)-Methyl 2-ethoxy-1-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-1H-benzo[d]iMidazole-7-carboxylate;(Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-ca;Methyl 2-ethoxy-1-((2'-(N-hydroxycarbamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole;InterMediate of Azilsartan;Methyl 2-Ethoxy-1-[[2'-(hydroxyamidino)biphenyl-4-yl]-1H-benzimidazole-7-carbo-xylate;methyl (Z)-2-ethoxy-1-((2'-(N'-hydroxycar
bamimidoyl)-[1,1'-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate;2-Ethoxy-1-｛[2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl]Methyl｝-1H-benzo[d]iMidazole-7 -carboxylic acid Methyl ester | | CAS: | 147403-65-4 | | MF: | C25H24N4O4 | | MW: | 444.48 | | EINECS: | 692-067-3 | | Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 147403-65-4.mol | ![(Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate Structure](CAS/GIF/147403-65-4.gif) |
| | (Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate Chemical Properties |
| Melting point | 207-209℃ | | Boiling point | 657.2±65.0 °C(Predicted) | | density | 1.29 | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 6.77±0.69(Predicted) | | color | White to Pale Yellow | | InChI | InChI=1S/C25H24N4O4/c1-3-33-25-27-22-10-6-9-21(24(30)32-2)23(22)29(25)16-17-11-13-18(14-12-17)20-8-5-4-7-19(20)15-26-28-31/h4-15,28,31H,3,16H2,1-2H3 | | InChIKey | STYVDYYCTQZFDE-UHFFFAOYSA-N | | SMILES | C1(OCC)N(CC2=CC=C(C3=CC=CC=C3C=NNO)C=C2)C2=C(C(OC)=O)C=CC=C2N=1 |
| | (Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate Usage And Synthesis |
| Chemical Properties | White Solid | | Uses | Azilsartan (A926900) derivative. Intermediate in the synthesis of angiotensin II receptor antagonist. | | Synthesis | N,N-dimethylacetamide (2 L) and water (16 L) were added to the reaction flask, followed by hydroxylamine hydrochloride (3.37 kg, 48.6 mol) and sodium carbonate (5.15 kg, 48.6 mol). Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (2 kg, 4.86 mol) was added to the reaction mixture and the reaction was carried out at 70 °C for 18 hours. After completion of the reaction, it was cooled to room temperature and water (2 L) was added to promote precipitation of the product. The precipitate was collected by filtration to afford methyl 2-ethoxy-1-[2'-(N'-hydroxyformamidino)biphenyl-4-yl]-1H-benzimidazole-7-carboxylate (1.94 kg, 37.70 mol). The product was analyzed by HPLC (refer to Example 1 conditions) with 98.9% purity and 90% yield. | | References | [1] Patent: CN103408500, 2016, B. Location in patent: Paragraph 0026; 0046-0047
[2] Patent: WO2013/114305, 2013, A1. Location in patent: Page/Page column 15; 16
[3] Organic Process Research and Development, 2015, vol. 19, # 4, p. 514 - 519
[4] Organic Process Research and Development, 2013, vol. 17, # 1, p. 77 - 86
[5] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 4, p. 929 - 936 |
| | (Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate Preparation Products And Raw materials |
| Raw materials | Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate-->Azilsartan-->1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-[[2'-[imino[[(methoxycarbonyl)oxy]amino]methyl][1,1'-biphenyl]-4-yl]methyl]-, methyl ester-->Hydroxylamine hydrochloride-->Sodium bicarbonate-->Water-->N,N-Dimethylacetamide | | Preparation Products | Azilsartan iMpurity I-->Azilsartan iMpurity A-->1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, Methyl ester |
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