Potassium Carbonate → HCID 58042456, compound

HRID 2048015Notes

Reaction equation

HRID 2048015 reaction equation
[F:1][C:2]1[CH:14]=[C:13](F)[C:12]([F:16])=[CH:11][C:3]=1[C:4]([NH:6][S:7]([CH3:10])(=[O:9])=[O:8])=[O:5].[Cl:17][C:18]1[CH:19]=[C:20]([OH:29])[CH:21]=[N:22][C:23]=1[O:24][CH:25]1[CH2:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[Cl:17][C:18]1[CH:19]=[C:20]([O:29][C:13]2[C:12]([F:16])=[CH:11][C:3]([C:4]([NH:6][S:7]([CH3:10])(=[O:9])=[O:8])=[O:5])=[C:2]([F:1])[CH:14]=2)[CH:21]=[N:22][C:23]=1[O:24][CH:25]1[CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 580424352,4,5-trifluoro-N-(methylsulfonyl)benzamideHCID 58042458HCID 58042458, compound

Product 1

HCID 58042456HCID 58042456, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2,4,5-trifluoro-N-(methylsulfonyl)benzamide (Preparation 27, 0.317 g, 1.25 mmol), 5-chloro-6-cyclobutoxypyridin-3-ol (Preparation 19, 0.250 g, 1.25 mmol) and potassium carbonate (0.346 g, 2.50 mmol) were suspended in DMSO (16 mL) and heated at 90° C. for 48 hours. The reaction was diluted with water (50 mL) and extracted with EtOAc (3×20 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with 20% EtOAc (with 0.5% AcOH) in heptane to afford the title compound as a white solid (64 mg, 12%):

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by silica gel chromatography
  6. washeluting with 20% EtOAc (with 0.5% AcOH) in heptane

Sources & evidence

ORD record
ord-3c7df2788c414a5997e7ad8589fad296
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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