HCID 178486439, compound → HCID 178486437, compound

Participants

Reaction Steps

A mixture of 0.1 gram (0.0004 mole) of {[4-(6-methoxy-7-methyl(2H-chromen-4-yl)imidazolyl]sulfonyl}dimethylamine (ix), 0.01 gram (catalyst) of 10% palladium on carbon, and 0.005 gram (catalyst) of 5% platinum on carbon in 75 mL of methanol was subjected to hydrogenation conditions during a two hour period using a Parr hydrogenator. After this time, the reaction mixture was passed through a column of silica gel to remove the catalysts. The eluate was concentrated under reduced pressure to a residue. An NMR spectrum of the residue was consistent with the proposed structure. The reaction was repeated on a larger scale, using 1.1 grams (0.0044 mole) of {[4-(6-methoxy-7-methyl(2H-chromen-4-yl)imidazolyl]sulfonyl}dimethylamine. The reaction product was purified by column chromatography on Grade II alumina (basic-3% water) using methylene chloride and a 99.5:0.5 mixture of methylene chloride and methanol, respectively, as eluants. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 0.38 gram of the subject compound, mp 138-139° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence