HCID 178486439, compound → HCID 178486437, compound

HRID 499030Notes

Reaction equation

HRID 499030 reaction equation
O[C:2]1([C:15]2[N:16]=[C:17]([S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[NH:18][CH:19]=2)[C:11]2[C:6](=[CH:7][C:8]([CH3:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[O:5][CH2:4][CH2:3]1>[Pd].[Pt].CO>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[CH3:14])[O:5][CH2:4][CH2:3][CH:2]2[C:15]1[N:16]=[C:17]([S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])[NH:18][CH:19]=1

Participants

5

Reactant 1

HCID 178486439HCID 178486439, compound

Product 1

HCID 178486437HCID 178486437, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  1. customto remove the catalysts
  2. concentrationThe eluate was concentrated under reduced pressure to a residue
  3. customThe reaction product was purified by column chromatography on Grade II alumina (basic-3% water)
  4. additiona 99.5:0.5 mixture of methylene chloride and methanol
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1889cb8555914066abf00b22570cd1ef
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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