Potassium Carbonate → HCID 19799241, compound

HRID 2081219Notes

Reaction equation

HRID 2081219 reaction equation
[CH3:1][N:2]([CH3:33])[S:3]([N:6]1[C:10]([CH3:11])=[C:9]([CH2:12][N:13]([CH2:20][CH2:21][C:22]2[N:23]([CH3:32])[C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])C(=O)C(F)(F)F)[N:8]=[CH:7]1)(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[F:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[N:23]([CH3:32])[C:22]([CH2:21][CH2:20][NH:13][CH2:12][C:9]1[N:8]=[CH:7][N:6]([S:3]([N:2]([CH3:33])[CH3:1])(=[O:4])=[O:5])[C:10]=1[CH3:11])=[CH:30]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 19799276HCID 19799276, compound

Product 1

HCID 19799241HCID 19799241, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[[1-[(dimethylamino)sulphonyl]-5-methyl-1H-imidazol -4-yl]methyl]-2,2,2-trifluoro-N-[2-(7-fluoro-1-methyl-1H-indol-2-yl)-ethyl]acetamide (230 mg) in methanol (10 ml) was added potassium carbonate (350 mg), and the mixture was heated at reflux for 2 h. The mixture was then diluted with ethyl acetate (100 ml), washed with 8% sodium bicarbonate solution (100 ml), dried, and evaporated in vacuo to leave an oil. This was purified by FCC eluting with System A (200:8:1) to give the title compound (110 mg) as a solid, m.p. 114°-115.5°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. washwashed with 8% sodium bicarbonate solution (100 ml)
  4. customdried
  5. customevaporated in vacuo
  6. customto leave an oil
  7. customThis was purified by FCC
  8. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-3587765079e24d6d9d53775e66c97e69
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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