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

HRID 453115
Notes
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Reaction equation

HRID 453115 reaction equation
Br[CH2:2][C:3]1[S:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[O:15][CH3:16])[N:4]=1.[F:17][C:18]1[C:26]([OH:27])=[CH:25][CH:24]=[C:23]([F:28])[C:19]=1[C:20]([NH2:22])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]=[C:3]([CH2:2][O:27][C:26]3[C:18]([F:17])=[C:19]([C:23]([F:28])=[CH:24][CH:25]=3)[C:20]([NH2:22])=[O:21])[S:7][N:6]=2)=[C:9]([O:15][CH3:16])[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 451201362,6-Difluoro-3-hydroxybenzamideHCID 595495315-(Bromomethyl)-3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazole

Product 1

HCID 252311103-((3-(4-Chloro-2-methoxyphenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamideYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 5-(bromomethyl)-3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazole (0.06 g, 0.19 mmol) in DMF (4 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.029 g, 0.17 mmol) and potassium carbonate (0.091 g, 0.66 mmol). The reaction mixture was stirred at room temperature for 90 min 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, 100% EtOAc) to get the desired product (0.02 g, 26%).

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, 100% EtOAc)

Sources & evidence

ORD record
ord-15cb175ff67f4d0eabeabe803efb152d
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492414B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes