Reaktionsgleichung
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:19](O)([C:21]([F:24])([F:23])[F:22])=O>>[N:13]1([C:9]2[CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]3[NH:1][C:19]([C:21]([F:24])([F:23])[F:22])=[N:12][C:11]=3[CH:10]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1Komponenten
Versuchsvorschrift
A mixture of methyl 2,3-diamino-5-(4-morpholinyl)benzoate (4.0 g) in CF3COOH (20 mL) was heated at reflux temperature for 8 h. When TLC analysis indicated consumption of starting material, the mixture was cooled to room temperature and the solvent was removed in-vacuo. The residue was diluted with aqueous NaHCO3 and extracted with EtOAc (250 mL×3). The combined organic layers were washed with brine (250 mL×2), dried over anhydrous Na2SO4. After filtration, the solvent was removed by rotary evaporator. The residue was then purified by silica gel chromatography eluted with EtOAc:petroleum ether=1:4 to afford the desired product as a pale solid. (4.3 g, 82.7%). 1H NMR (300 MHz, DMSO-d6): δ ppm 13.47 (s, 1H), 7.71 (s, 1H), 7.56 (s, 1H), 3.96 (s, 3H), 3.79 (t, 4H, J=4.5 Hz), 3.17 (s, 4H). LC-MS: m/e=330.1 [M+1]+.
Aufarbeitung
- temperaturewas heated
- temperatureat reflux temperature for 8 h
- customconsumption of starting material
- customthe solvent was removed in-vacuo
- additionThe residue was diluted with aqueous NaHCO3
- extractionextracted with EtOAc (250 mL×3)
- washThe combined organic layers were washed with brine (250 mL×2)
- dry with materialdried over anhydrous Na2SO4
- filtrationAfter filtration
- customthe solvent was removed by rotary evaporator
- customThe residue was then purified by silica gel chromatography
- washeluted with EtOAc
Quellen und Nachweise
- ORD-Eintrag
- ord-c497d058a0b34b9f8363e1ebb4347e19
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08541411B2
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