Hydrochloric Acid → HCID 69000159, compound

HRID 1951607Notes

Reaction equation

HRID 1951607 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[S:7][C:8]=1[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])(=[O:22])=[O:21])=[CH:15][CH:14]=1)=[O:12])([CH3:3])[CH3:2].IC.[C:44](=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH:1]([C:4]1[N:5]=[C:6]([C:32]2[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:36][CH:37]=2)[S:7][C:8]=1[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:44])[S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])(=[O:21])=[O:22])=[CH:15][CH:14]=1)=[O:12])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69003325HCID 69003325, compound

Product 1

HCID 69000159HCID 69000159, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The obtained N-[4-[3-[4-isopropyl-2-[4-(trifluoromethyl)phenyl]thiazol-5-yl]propionyl]phenyl]-2-nitrobenzenesulfonamide (265 mg, 0.439 mmol) was dissolved in anhydrous dimethylformamide (10 mL). Iodomethane (30 μL, 0.483 mmol) and potassium carbonate (121 mg, 0.875 mmol) were added to the solution. The mixture was stirred at room temperature for 16 hours. The mixture was neutralized with 0.2 N aqueous solution of hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and dried with anhydrous sodium sulfate to remove the solvent. The obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (7:3, v/v) to give the desired compound (230 mg) as yellow oil (yield 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customto remove the solvent
  5. customThe obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (7:3

Sources & evidence

ORD record
ord-92450d20153541ba9a71ec6463106cc9
Source dataset
uspto-grants-2013_03
Patent number
US08404726B2

Reaction notes

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