Potassium Carbonate → 2,6-Difluoro-3-[3-(4-methoxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-benzamide

HRID 453100Notes

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-bromomethyl-3-(4-methoxyphenyl)-[1,2,4]thiadiazole (0.048 g, 0.15 mmol) in DMF (2 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.027 g, 0.15 mmol) and potassium carbonate (0.76 g, 0.55 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 (0.011 g, 30%).

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-3e4c7f56f18c4ccb8d3204e62967f375
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492414B2

Reaction notes

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