Potassium Carbonate → HCID 136146568, compound

HRID 1963009Notes

Reaction equation

Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:4]=1.[F:15][C:16]1[C:21]([OH:22])=[CH:20][CH:19]=[C:18]([F:23])[C:17]=1[C:24]1[NH:28][C:27](=[O:29])[O:26][N:25]=1.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:22][C:21]3[C:16]([F:15])=[C:17]([C:24]4[NH:28][C:27](=[O:29])[O:26][N:25]=4)[C:18]([F:23])=[CH:19][CH:20]=3)[O:7][N:6]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-chloromethyl-3-(4-chlorophenyl)-[1,2,4]oxadiazole (0.080 g, 0.35 mmol) in anhydrous DMF (2 ml) was added 3-(2,6-difluoro-3-hydroxyphenyl)-4H-[1,2,4]oxadiazol-5-one (0.075 g, 0.35 mmol) and potassium carbonate (0.17 g, 1.22 mmol) was added. The reaction mixture was stirred at 25° C. for 24 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure, added water and extracted with EtOAc (3×50 ml). The combined organics was washed with water, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica (60-120 M) using ethyl acetate/hexane (45:55) as the eluent to provide the title compound as off white solid (0.0088 g, 6%).

Workup

additionwas added
customAfter the completion of the reaction (TLC monitoring)
customthe reaction mixture was evaporated to dryness under reduced pressure
additionadded water
extractionextracted with EtOAc (3×50 ml)
washThe combined organics was washed with water
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified over silica (60-120 M)

Sources & evidence

ORD record: ord-3ff973275b42427b97153eb289a95db7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415383B2

Reaction notes

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