Chloroacetone → HCID 16073184, compound

HRID 915511Notes

Reaction equation

HRID 915511 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:19][CH:20]([CH3:22])[CH3:21])[C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][C:8]=2[O:7][C:6]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:37][C:38](=[O:40])[CH3:39]>CC(=O)CC>[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:19][CH:20]([CH3:22])[CH3:21])[C:12]([N:14]([S:15]([CH3:18])(=[O:16])=[O:17])[CH2:37][C:38](=[O:40])[CH3:39])=[CH:13][C:8]=2[O:7][C:6]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[O:4]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 10409873HCID 10409873, compound

Product 1

HCID 16073184HCID 16073184, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Fluoro-phenyl)-5-isopropoxy-6-methanesulfonylamino-benzofuran-3-carboxylic acid methylamide (0.093 g, 0.221 mmol, which can be prepared according to one of the procedures described in Example 21) was dissolved in 2-butanone (20 mL). Potassium carbonate (0.20 g, 1.45 mmol) and chloroacetone (0.10 mL, 1.25 mmol) were added at 20° C. The reaction mixture was refluxed for 2 hours, cooled to room temperature and concentrated. The crude product was dissolved in ethyl acetate and washed with 1M hydrochloric acid. The organic layer was concentrated, and the product was purified by flash chromatography (silica gel, ethyl acetate/hexanes gradient) to provide 99 mg (94%) of the title compound as a white solid

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. concentrationconcentrated
  3. dissolutionThe crude product was dissolved in ethyl acetate
  4. washwashed with 1M hydrochloric acid
  5. concentrationThe organic layer was concentrated
  6. customthe product was purified by flash chromatography (silica gel, ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-0a00eef7e6bd49b3b5f52846f46a4348
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

Loading…