Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[CH2:10]([N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:28]([C:30]1[CH:31]=[N:32][CH:33]=CC=1)#[N:29].B(O)(O)C1C=CC=C(F)C=1>ClCCl.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:33]2[N:29]=[CH:28][C:30]([C:21]3[NH:17][C:18]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)=[N:19][CH:20]=3)=[CH:31][N:32]=2)[CH:2]=1.[CH2:10]([N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1Komponenten
Edukt 4
Produkt 2
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The title compound was prepared by the method described in Example 1, except that (i) commercially available 3-pyridyl boronic acid was used instead of benzene boronic acid in Step A, and (ii) 3-(1-benzyl-1H-imidazol-2-yl)pyridine was used instead of 1-benzyl-2-phenyl-1H-imidazole in Step C. 3-(1-Benzyl-1H-imidazol-2-yl)pyridine was prepared by the method described in Example 8, Steps A and B except the commercially available 3-cyanopyridine was used instead of 3-fluorobenzonitrile; Rf 0.35 with 92.5:7.5 v/v dichloromethane-methanol; melting point 299° C.; 1H-NMR (400 MHz; DMSO-d6) δ 9.52 (s, 1H), 9.35 (s, 2H), 9.21 (s, 1H), 8.72-8.65 (m, 2H), 8.60-8.56 (m, 1H), 8.37-8.32 (m, 1H), 8.15 (s, 1H), 7.58-7.50 (m, 2H); LC/MS (ESI+) m/z 301.1 (M+1); H-PGDS FPBA IC50: 1.3 μM.
Quellen und Nachweise
- ORD-Eintrag
- ord-fed8e7fb6661480d954605fc0cc8eb9c
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08536185B2
Verknüpfte Notizen
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