Hydrochloric Acid → HCID 22736767, Verbindung

HRID 50882

Reaktionsgleichung

Reaktionsgleichung von HRID 50882
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[CH3:15][C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1/[CH:18]=[CH:19]/[C:20]([Cl:22])=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:22].[CH3:15][C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1/[CH:18]=[CH:19]/[C:20]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 5706558(e)-3-o-Tolylacryloyl chlorideHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Produkt 1

HCID 22736767HCID 22736767, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-2-methylcinnamoyl chloride (Sekiya, T.; Hiranuma, H.; Hata, S.; Mizogami, S.; Hanazuka, M.; Yamada, S. J. Med. Chem., 1983, 26, 411) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate/ethanol yielded the titled compound. MW: 347.85; mp: 212.0-215.0° C.; 1H-NMR (CDCl3) δ: 9.26 (1H, d, J=16.1 Hz), 8.89-8.83 (1H, m), 8.24-8.12 (2H, m), 7.72-7.64 (2H, m), 7.59-7.43 (4H, m), 7.43-7.11 (3H, m), 6.92 (1H, d, J=16.1 Hz), 2.70 (3H, s).

Aufarbeitung

  1. concentrationConcentration and recrystallization from ethyl acetate/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-788d893663f043699acd01d7179b5f29
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713482B2

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