Potassium Carbonate → 3-((3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide

HRID 453122Notes

Reaction equation

HRID 453122 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21]Br)[S:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[C:32]([OH:33])=[CH:31][CH:30]=[C:29]([F:34])[C:25]=1[C:26]([NH2:28])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21][O:33][C:32]2[C:24]([F:23])=[C:25]([C:29]([F:34])=[CH:30][CH:31]=2)[C:26]([NH2:28])=[O:27])[S:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 451201362,6-Difluoro-3-hydroxybenzamideHCID 595495203-(2-(Benzyloxy)-4-chlorophenyl)-5-(bromomethyl)-1,2,4-thiadiazole

Product 1

HCID 595495353-((3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamideYield 33.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-(benzyloxy)-4-chlorophenyl)-5-(bromomethyl)-1,2,4-thiadiazole (0.33 g, 0.83 mmol) in DMF (10 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.13 g, 0.75 mmol) and potassium carbonate (0.403 g, 2.92 mmol). The reaction mixture was stirred at room temperature for 16 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 25 ml water and extracted with ethyl acetate (3×25 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 40% EtOAc-Hexane) to get the desired product (0.123 g, 30%).

Workup

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe reaction mixture was evaporated to dryness under vacuum
  3. additionadded 25 ml water
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude residue was purified over silica gel (100-200 M, 40% EtOAc-Hexane)

Sources & evidence

ORD record
ord-b8b40631b5bc4c6095265de673faeb39
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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