Benzoate → HCID 12017704, compound

HRID 1006546Notes

Reaction equation

HRID 1006546 reaction equation
[C:1]([O-])(=O)[C:2]1C=CC=C[CH:3]=1.[C:10]1([S:16]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=2[NH:30][CH2:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[H-].[Na+].[CH3:44]I>CN(C=O)C>[CH3:44][N:30]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:40][CH:41]=1)[C:21]1[CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=[CH:25][C:20]=1[N:19]([S:16]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:17])=[O:18])[CH:2]([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 242BenzoateHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22671955HCID 22671955, compound

Product 1

HCID 12017704HCID 12017704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-[2-(N-isopropyl-phenylsulfonylamino)-5-trifluoromethyl-phenyl]aminomethyl]benzoate (200 mg) prepared by the same procedure as Example 17 by using methyl 4-(2-phenylsulfonylamino-5-trifluoromethyl-phenylaminomethyl)benzoate (prepared in Example 27) was dissolved in DMF (5 ml). Sodium hydride (64 mg) and methyl iodide (200 μl) were added thereto. The mixture was stirred for 24 hours at 60° C. The reaction mixture was extracted with H2O-AcOEt, washed, dried over, filtered and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane:AcOEt=5:1) to give the title compound (105 mg) having the following physical data.

Workup

  1. extractionThe reaction mixture was extracted with H2O-AcOEt
  2. washwashed
  3. customdried over,
  4. filtrationfiltered
  5. concentrationconcentrated under the reduced pressure
  6. customThe residue was purified on silica gel column chromatography (hexane:AcOEt=5:1)

Sources & evidence

ORD record
ord-b291a97798344867b87aafa567bda363
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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