Potassium Hydroxide → HCID 59191240, compound

HRID 626008Notes

Reaction equation

HRID 626008 reaction equation
CS([O:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][CH3:14])[CH:9]=[CH:8][C:7]=1[O:15][C:16]1[CH:17]=[N:18][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:20][CH:21]=1)(=O)=O.[OH-].[K+]>O>[OH:5][C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][CH3:14])[CH:9]=[CH:8][C:7]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:24])=[O:25])=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59191416HCID 59191416, compound

Product 1

HCID 59191240HCID 59191240, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-({6-[(methylsulfonyl)amino]pyridin-3-yl}oxy)-5-propylphenyl methanesulfonate (0.09 mmol; 30 mg), under argon, in water (0.5 mL), was added KOH (0.26 mmol; 15 mg). The reaction mixture was refluxed for 4 hr. After quenching with NH4Cl (1 mL), extraction with ethyl acetate (3*3 mL), combined organic phases were washed with water (3 mL), dried over MgSO4, concentrated in vacuo, to yield the title compound as a white solid (37 mg; 0.09 mmol; 77%).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hr
  2. customAfter quenching with NH4Cl (1 mL), extraction with ethyl acetate (3*3 mL)
  3. washwere washed with water (3 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0afafd311ae2422e9680d6b59baa9e54
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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