Trifluoroacetic acid → HCID 19972885, compound

HRID 1451929Notes

Reaction equation

HRID 1451929 reaction equation
[C:1]1([S:11]([NH:14][CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2([C:37]2[CH:38]=[CH:39][C:40]3[N:41]([CH:43]=[CH:44][N:45]=3)[CH:42]=2)[C:24]([S:27]CC2C=CC(OC)=CC=2)=[N:25][CH3:26])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:1]1([S:11]([NH:14][CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2([C:37]2[CH:38]=[CH:39][C:40]3[N:41]([CH:43]=[CH:44][N:45]=3)[CH:42]=2)[C:24](=[S:27])[NH:25][CH3:26])(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 10340Sodium CarbonateHCID 19972903HCID 19972903, compound

Product 1

HCID 19972885HCID 19972885, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising 0.4 g of the 2-(2-(1-naphthalenesulfonamido)ethoxy)-1-(imidazo[1,2-a]pyridin-6-yl)-1-((4-methoxybenzylthio)(methylimino)methyl)cyclohexane, 0.5 ml of anisole, 5 ml of trifluoroacetic acid and 5 ml of dichloromethane was stirred under cooling with ice for 1.5 hours, followed by the addition of ice-water. The resulting mixture was alkalinized with sodium carbonate and extracted with chloroform. The chloroform phase was dried over anhydrous magnesium sulfate and ditilled to remove the solvent. The residue was purified by silica gel column chromatography (solvent: a 80:1 dichloromethane/methanol mixture) and crystallized from ethyl acetate/n-hexane to give 0.21 g of the title compound as a white powder (yield: 65%).

Workup

  1. temperatureunder cooling with ice for 1.5 hours
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform phase was dried over anhydrous magnesium sulfate
  4. customto remove the solvent
  5. customThe residue was purified by silica gel column chromatography (solvent
  6. customa 80:1 dichloromethane/methanol mixture) and crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-26d493f2f24647828192745afeee143b
Source dataset
uspto-grants-1997_02
Patent number
US05605907

Reaction notes

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