Candesartan Cilexetil → 2-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid

HRID 549973

Reaktionsgleichung

Reaktionsgleichung von HRID 549973
[CH3:1][CH2:2][O:3][C:4]1[N:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[N:30]=[N:29][NH:28][N:27]=3)=[CH:18][CH:19]=2)[C:11]2[C:10]([C:31]([O:33]C(OC(OC3CCCCC3)=O)C)=[O:32])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1.C(OC1NC2C(CC3C=CC(C4C=CC=CC=4C4NN=NN=4)=CC=3)=CC=C(C(O)=O)C=2N=1)C.[C:79](Cl)([C:92]1[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=1)([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1>>[CH2:2]([O:3][C:4]1[N:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[N:27]([C:79]([C:80]4[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=4)([C:92]4[CH:93]=[CH:94][CH:95]=[CH:96][CH:97]=4)[C:86]4[CH:87]=[CH:88][CH:89]=[CH:90][CH:91]=4)[N:28]=[N:29][N:30]=3)=[CH:18][CH:19]=2)[C:11]2[C:10]([C:31]([OH:33])=[O:32])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1)[CH3:1]

Komponenten

4

Edukt 3

HCID 2540Candesartan CilexetilHCID 6456Trityl chlorideHCID 178467389HCID 178467389, Verbindung

Produkt 1

HCID 103125632-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid

Versuchsvorschrift

U.S. Pat. No. 5,196,444 discloses Candesartan cilexetil and a process for its preparation by the reaction of 2-ethoxy-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid with trityl chloride in presence of triethyl amine in methylene chloride and purification by column chromatography gives 2-ethoxy-1-[[2′-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid, which upon condensation with cyclohexyl 1-iodoethyl carbonate in presence of potassium carbonate in DMF followed by purification with column chromatography gives a colorless powder which is recrystallized in ethanol yields ‘C’ type crystals of Candesartan cilexitil.

Aufarbeitung

  1. customin presence of triethyl amine in methylene chloride and purification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-61533736cb9344ae8332c8128e9f2977
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943780B2

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