Potassium Iodide → HCID 59309838, compound

HRID 1513048Notes

Reaction equation

HRID 1513048 reaction equation
[C:1]([C:4]1[N:9]=[C:8]2[N:10]([C:14]3[CH:19]=[C:18]([S:20]([C:23]([CH3:31])([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:24])(=[O:22])=[O:21])[C:17]([O:32][CH3:33])=[CH:16][C:15]=3[Cl:34])[C:11](=[O:13])[NH:12][C:7]2=[C:6]([CH3:35])[CH:5]=1)([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:44]([O:46][C:47]([O:49][CH:50](Cl)[CH3:51])=[O:48])[CH3:45]>CN(C)C=O.C(OCC)(=O)C>[Cl:34][C:15]1[CH:16]=[C:17]([O:32][CH3:33])[C:18]([S:20]([C:23]([CH3:24])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:31])(=[O:22])=[O:21])=[CH:19][C:14]=1[N:10]1[C:8]2=[N:9][C:4]([C:1]([O:3][CH:44]([O:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH3:45])=[O:2])=[CH:5][C:6]([CH3:35])=[C:7]2[NH:12][C:11]1=[O:13]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 59309931HCID 59309931, compound

Product 1

HCID 59309838HCID 59309838, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 5-carboxy-3-[2-chloro-4-methoxy-5-(1-methyl-1-phenyl-ethylsulfonyl)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (49 mg), potassium carbonate (17 mg) and potassium iodide (8 mg) in N,N-dimethylformamide (1 mL) was added 1-ethoxycarbonyloxyethyl chloride (0.015 mL), and the mixture was stirred at 60° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/2) to give the title compound (29 mg).

Workup

  1. washthe resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/2)

Sources & evidence

ORD record
ord-b2aecf17faa141aa97b673ef668cc1ad
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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