Methanol → N-[3,5-Bis(trifluoromethyl)benzyl]-N-methyl-2-methylthio-4-phenyl-3-quinolinecarboxamide

HRID 374995Notes

Reaction equation

HRID 374995 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH3:27])[C:8]([C:10]1[C:11](Cl)=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9].CO.C(S)[CH2:40][S:41]([O-])(=O)=O.[Na+]>C1COCC1.O>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH3:27])[C:8]([C:10]1[C:11]([S:41][CH3:40])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 21463112N-[3,5-Bis(trifluoromethyl)benzyl]-2-chloro-N-methyl-4-phenyl-3-quinolinecarboxamideHCID 23662354Mesna

Product 1

HCID 21463181N-[3,5-Bis(trifluoromethyl)benzyl]-N-methyl-2-methylthio-4-phenyl-3-quinolinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in Example 269 (100 mg) in THF (6 ml)-methanol (2 ml) was added 15% MeSNa in water (4 ml), and the mixture was stirred for 8 hours with heating under reflux. The solvent was evaporated and the residue was dissolved in ethyl acetate. The solution was washed with water, dried and evaporated to yield the title compound as colorless crystals (55 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-7529599c4d144de69a3dc42e3c245890
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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