Ammonia → 6-Chloro-3-methyl-3,4,9,10-tetrahydro-2,3,4,9-tetraaza-benzo[f]azulene

To a suspension of 6-chloro-3-methyl-4,9-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-10-one from Example E1.3 (5.56 g, 22.4 mmol) in anhydrous THF (200 ml) at 0° C. was added lithium aluminium hydride (4.24 g, 112 mmol), and the resulting suspension was heated at reflux for 18 h, then allowed to cool to room temperature. A further portion of lithium aluminium hydride (4.24 g, 112 mmol) was added, and the mixture was heated at re-flux for 18 h. The mixture was cooled to 0° C., 35% ammonia solution (10 ml) was added dropwise over 15 min and the mixture was stirred at room temperature for 30 min. The resulting suspension was filtered through Celite® filter agent and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 0.5% 35% ammonia:5% methanol:dichloromethane) to yield the title compound (3.88 g, 74%).

1. temperaturethe resulting suspension was heated
2. temperatureat reflux for 18 h
3. temperaturethe mixture was heated at re-flux for 18 h
4. temperatureThe mixture was cooled to 0° C.
5. filtrationThe resulting suspension was filtered through Celite®
6. filtrationfilter agent
7. concentrationthe filtrate concentrated in vacuo
8. customThe residue was purified by flash chromatography on silica gel (eluant; 0.5% 35% ammonia:5% methanol:dichloromethane)

ORD record

ord-023d59e5969b40b58c1e5daf88715f5f

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202858B2