Potassium Carbonate → HCID 25231108, compound
Reaction equation
Br[CH2:2][C:3]1[S:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[N:4]=1.[F:19][C:20]1[C:28]([OH:29])=[CH:27][CH:26]=[C:25]([F:30])[C:21]=1[C:22]([NH2:24])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:19][C:20]1[C:28]([O:29][CH2:2][C:3]2[S:7][N:6]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=3)[N:4]=2)=[CH:27][CH:26]=[C:25]([F:30])[C:21]=1[C:22]([NH2:24])=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 5-bromomethyl-3-(4-trifluoromethoxyphenyl)-[1,2,4]thiadiazole (0.11 g, 0.32 mmol) in DMF (5 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.056 g, 0.32 mmol) and potassium carbonate (0.16 g, 1.13 mmol). The reaction mixture was stirred at 25° C. for 12 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 30 ml water and extracted with ethyl acetate (3×20 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, 50% EtOAc-Hexane) to get the desired product (0.013 g, 9%).
Workup
- customAfter the completion of the reaction (TLC monitoring)
- customthe reaction mixture was evaporated to dryness under vacuum
- additionadded 30 ml water
- extractionextracted with ethyl acetate (3×20 ml)
- dry with materialThe combined organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe crude residue was purified over silica gel (100-200 M, 50% EtOAc-Hexane)
Sources & evidence
- ORD record
- ord-e28d232e27e1494ba6cc10903fbda769
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492414B2
Reaction notes
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