Isopropyl isocyanate → tert-Butyl (2-(7-(2-fluoro-4-(3-isopropylureido)phenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl(2-methoxyethyl)carbamate
Reaktionsgleichung
[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:12][C:13]1[N:17]([CH3:18])[C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=3[F:36])[CH:20]=2)=[N:15][CH:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[N:38]([CH:41]([CH3:43])[CH3:42])=[C:39]=[O:40].CC(=O)OCC.CCCCCC>CO.CC(=O)OCC>[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:12][C:13]1[N:17]([CH3:18])[C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:39]([NH:38][CH:41]([CH3:43])[CH3:42])=[O:40])=[CH:31][C:30]=3[F:36])[CH:20]=2)=[N:15][CH:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:2])[CH3:3]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
The reaction mixture of aniline 46 (200 mg, 0.379 mmol) and 2-isocyanatopropane (64.5 mg, 0.758 mmol) was heated to 100° C. for 15 min in a microwave reactor. The reaction mixture was loaded directly into Biotage (Silicycle, HR, 12 g column, 50-100% EA/Hexane, then MeOH/EA, 0-20%). The collected fractions afforded the desired product 314 (150 mg, 0.245 mmol, 64.6% yield) as a white solid. MS: 613(MH)+, very weak signal.
Quellen und Nachweise
- ORD-Eintrag
- ord-f19158266dc1440f8e4fa56fbafa2a3c
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08759522B2
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