Water → HCID 58499779, compound

HRID 910268Notes

Reaction equation

HRID 910268 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].CI.[Cl:9][C:10]1[CH:11]=[C:12]([S:17]([NH:20][C@@H:21]([C:23]2[N:27]([CH2:28][CH3:29])[C:26]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[N:25][N:24]=2)[CH3:22])(=[O:19])=[O:18])[CH:13]=[CH:14][C:15]=1[Cl:16].O>CN(C)C=O>[Cl:9][C:10]1[CH:11]=[C:12]([S:17]([N:20]([C@@H:21]([C:23]2[N:27]([CH2:28][CH3:29])[C:26]([O:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)=[N:25][N:24]=2)[CH3:22])[CH3:1])(=[O:18])=[O:19])[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24859104HCID 24859104, compound

Product 1

HCID 58499779HCID 58499779, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (78 mg) and MeI (0.022 ml) were added at room temperature to a solution of Compound 12 (150 mg) of Example 1 in dimethylformamide (2.0 ml), and the mixture was stirred at room temperature for three hours. Water was added to the reaction solution, and the mixture was extracted with a mixed solution of methanol/chloroform (methanol/chloroform=1/4). The resulting organic layer was washed with saturated aqueous sodium chloride, dried (MgSO4), filtered, and evaporated under reduced pressure to remove the solvent. After eluting the residue with a mixed solvent of ethyl acetate and hexane, the resulting elute was purified by column chromatography (acidic OH SiO2, ethyl acetate/hexane=50-99%, methanol/chloroform=0-10%) and then recrystallized (ethyl acetate-hexane) to give 111 mg of the titled compound as a colorless powdered compound.

Workup

  1. extractionthe mixture was extracted with a mixed solution of methanol/chloroform (methanol/chloroform=1/4)
  2. washThe resulting organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. washAfter eluting the residue with a mixed solvent of ethyl acetate and hexane
  8. washthe resulting elute
  9. customwas purified by column chromatography (acidic OH SiO2, ethyl acetate/hexane=50-99%, methanol/chloroform=0-10%)
  10. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-a9411eb219654e8eb772bb23b0b42742
Source dataset
uspto-grants-2011_09
Patent number
US08022091B2

Reaction notes

Loading…