Trifluoroacetic acid → HCID 19973451, compound

HRID 1757118Notes

Reaction equation

HRID 1757118 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1([C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[CH:35][N:36]=2)[CH:33]=1)[C:15]([S:18]CC1C=CC(OC)=CC=1)=[N:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1([C:28]1[CH:29]=[CH:30][C:31]2[N:32]([CH:34]=[CH:35][N:36]=2)[CH:33]=1)[C:15](=[S:18])[NH:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 15290091HCID 15290091, compound

Product 1

HCID 19973451HCID 19973451, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg of the 2-benzyloxy-1-(imidazo[1,2-a]-pyridin-6-yl)-1-((4-methoxybenzylthio)(methylimino)methyl)cyclohexane prepared in the Preparative Example 4 was dissolved in 5 ml of dichloromethane, followed by the addition of 1 ml of anisole. The obtained mixture was cooled with ice, followed by the gradual addition of 5 ml of trifluoroacetic acid. The obtained mixture was stirred for one hour, followed by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was extracted with chloroform. The organic phase was dried over anhydrous sodium sulfate and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1)]. The obtained oil was crystallized from ether and the obtained crystal was recovered by filtration. Thus, 300 mg of the title compound was obtained as a white powder (yield 79%).

Workup

  1. temperatureThe obtained mixture was cooled with ice
  2. extractionThe obtained mixture was extracted with chloroform
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe obtained residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1)]
  7. customThe obtained oil was crystallized from ether
  8. filtrationthe obtained crystal was recovered by filtration

Sources & evidence

ORD record
ord-5d1c6e6164304365a10ee8d2b6367d46
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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