Reaktionsgleichung
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1N.[CH3:9][C:10]([CH:12]=[CH2:13])=O.ClC(Cl)=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:32][C:33]([NH2:35])=[S:34])[CH:23]=[CH:24][C:25]=1[N:26]1[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]1>>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[CH2:9][C:10]1[S:34][C:33]([NH:32][C:22]2[CH:23]=[CH:24][C:25]([N:26]3[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]3)=[C:20]([O:19][CH3:18])[CH:21]=2)=[N:35][C:12]=1[CH3:13]Komponenten
Versuchsvorschrift
The title compound was prepared in analogy to example 6 without purification of the intermediate from 128 mg (1 mmol) 2-chloroaniline 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 40 mg (47%) [5-(2-chloro-benzyl)-4-methyl-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a brown solid. MS ISP (m/e): 425.1/427.2 (100/44) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.15 (s, 1H), 7.63 (s, 1H), 7.53 (s, 1H), 7.47-7.22 (m, 6H), 7.01 (s, 1H), 4.07 (s, 2H), 3.77 (s, 3H), 2.25 (s, 3H), 2.14 (s, 3H).
Aufarbeitung
- customThe crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 40 mg (47%) [5-(2-chloro-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-5e4a7434469a47ef9731c2cb7c1d300e
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07910740B2
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