Cesium carbonate → HCID 73775728, compound

HRID 2207273Notes

Reaction equation

HRID 2207273 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[C:10]([C:12]3[CH:16]=[CH:15][O:14][CH:13]=3)[N:9]=[CH:8][C:7]=2[OH:17])=[CH:2]1.[C:18]([C:20]1[CH:21]=[C:22]([S:27]([NH:30][C:31]2[S:32][CH:33]=[CH:34][N:35]=2)(=[O:29])=[O:28])[CH:23]=[CH:24][C:25]=1F)#[N:19].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:18]([C:20]1[CH:21]=[C:22]([S:27]([NH:30][C:31]2[S:32][CH:33]=[CH:34][N:35]=2)(=[O:29])=[O:28])[CH:23]=[CH:24][C:25]=1[O:17][C:7]1[CH:8]=[N:9][C:10]([C:12]2[CH:16]=[CH:15][O:14][CH:13]=2)=[CH:11][C:6]=1[C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)#[N:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 580422683-Cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamideHCID 90101039HCID 90101039, compound

Product 1

HCID 73775728HCID 73775728, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20.0 mg of 4,6-di(furan-3-yl)pyridin-3-ol and 24.9 mg of 3-cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamide were dissolved in DMF, and 86.0 mg (3.0 eq) of Cs2CO3(86.0 mg, 3.0 eq) was added thereto. After reacting at room temperature for 2 hours, the resulting mixture was reacted at 60° C. for 16 hours. The solvent was removed by concentrating under reduced pressure. AS work-up with EA/H2O, the ethyl acetate layer was treated with magnesium sulfate, and concentrated under reduced pressure. The residue was separated by PLC (developing solvent, EA:n-Hex=1:4) to obtain 10.1 mg (24% yield) of the title compound.

Workup

  1. customthe resulting mixture was reacted at 60° C. for 16 hours
  2. customThe solvent was removed
  3. concentrationby concentrating under reduced pressure
  4. additionAS work-up with EA/H2O, the ethyl acetate layer was treated with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by PLC (developing solvent, EA:n-Hex=1:4)

Sources & evidence

ORD record
ord-6100c925aa684c8e92773c9fdc857b14
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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