Reaktionsgleichung
[C:1]([C:5]1[CH:11]=[CH:10][C:8](N)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12][C:13]([CH:15]=[CH2:16])=O.ClC(Cl)=O.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH:35][C:36]([NH2:38])=[S:37])[CH:26]=[CH:27][C:28]=1[N:29]1[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]1>>[C:1]([C:5]1[CH:11]=[CH:10][C:8]([CH2:12][C:13]2[S:37][C:36]([NH:35][C:25]3[CH:26]=[CH:27][C:28]([N:29]4[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]4)=[C:23]([O:22][CH3:21])[CH:24]=3)=[N:38][C:15]=2[CH3:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Komponenten
Versuchsvorschrift
The title compound was prepared in analogy to example 7 without purification of the intermediate from 149 mg (1 mmol) 4-tert-butylaniline and 421 mg (6 mmol) methyl vinylketone. The crude chloroketone was used without further purification in the next step with 53 mg (0.2 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 45 mg (50%) of [5-(4-tert-butyl-benzyl)-4-methyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a brown solid. MS ISP (m/e): 447.3 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.12 (s, 1H), 7.63 (s, 1H), 7.53 (s, 1H), 7.32 (d, 2H), 7.22 (s, 2H), 7.15 (d, 2H), 7.01 (s, 1H), 3.92 (s, 2H), 3.77 (s, 3H), 2.24 (s, 3H), 2.13 (s, 3H).
Aufarbeitung
- customThe crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 45 mg (50%) of [5-(4-tert-butyl-benzyl)-4-methyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a brown solid
Quellen und Nachweise
- ORD-Eintrag
- ord-650227d151cf424eb9a1698219a73e72
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07910740B2
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