Sodium hydride → HCID 44210827, compound

1-Methyl-1H-indole-3-carboxamide oxime (C. J. Swain et al, J.Med. Chem, 1991, 34, 147)(0.250 g, 1.33 mmol) was dissolved in dry THF (8 ml) with stirring and treated with ground 4A° molecular sieves (1 g), under nitrogen. After 30 minutes sodium hydride (80% dispersion in mineral oil) (0.044 g, 1.46 mmol) was added. The mixture was then heated to reflux, after 30 minutes, the mixture was allowed to cool momentarily, and a solution of ethyl-4-N-methylbutylaminobutyrate (0.293 g, 1.46 mmol) in dry THF (2 ml) was added. The mixture was then heated to reflux. After 6 h, the reaction mixture was allowed to cool, and was then filtered. The filter pad was then washed with THF (2×) and the filtrate evaporated under reduced pressure. The residue was then purified by silica-gel chromatography, eluting with ethyl acetate/methanol 20:1 to afford the title compound as a colourless oil (0.243 g, 56%), which was converted to its hydrochloride salt, m.pt, 174°-175° C.

1. additiontreated with ground 4A° molecular sieves (1 g), under nitrogen
2. temperatureThe mixture was then heated
3. temperatureto reflux, after 30 minutes
4. temperatureto cool momentarily
5. temperatureThe mixture was then heated to reflux
6. temperatureto cool
7. filtrationwas then filtered
8. washThe filter pad was then washed with THF (2×)
9. customthe filtrate evaporated under reduced pressure
10. customThe residue was then purified by silica-gel chromatography
11. washeluting with ethyl acetate/methanol 20:1

ORD record

ord-3de822bc2f174c7b8a572d51ec385848

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05492919