Potassium Carbonate → 3-[3-(4-Benzyloxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-2,6-difluorobenzamide

HRID 453108Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([CH2:20]Br)[S:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[C:31]([OH:32])=[CH:30][CH:29]=[C:28]([F:33])[C:24]=1[C:25]([NH2:27])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([CH2:20][O:32][C:31]3[C:23]([F:22])=[C:24]([C:28]([F:33])=[CH:29][CH:30]=3)[C:25]([NH2:27])=[O:26])[S:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(4-benzyloxyphenyl)-5-bromomethyl-[1,2,4]thiadiazole (0.04 g, 0.11 mmol) in DMF (2 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.017 g, 0.10 mmol) and potassium carbonate (0.53 g, 0.39 mmol). The reaction mixture was stirred at 25° C. overnight under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 20 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, 40% EtOAc-Hexane) to get the desired product (0.025 g, 50%). MS ES+ (454.13).

Workup

customAfter the completion of the reaction (TLC monitoring)
customthe reaction mixture was evaporated to dryness under vacuum
additionadded 20 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, 40% EtOAc-Hexane)

Sources & evidence

ORD record: ord-3c182c9dc88e4ac4b8fb42a9691f0a4c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492414B2

Reaction notes

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