Water → HCID 58158517, compound

HRID 2095757Notes

Reaction equation

HRID 2095757 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][C:10]=2[F:26])=[CH:4][CH:3]=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>N1C=CC=CC=1>[F:26][C:10]1[CH:11]=[C:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[CH:6]=[N:7][C:2]([NH:1][S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=2)(=[O:35])=[O:34])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 58158480HCID 58158480, compound

Product 1

HCID 58158517HCID 58158517, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of benzyl {4-[(6-aminopyridin-3-yl)oxy]-3-fluorophenyl}carbamate (28.2 g, 79.8 mmol) in pyridine (141 mL) was added p-toluenesulfonyl chloride (18.3 g, 98.5 mmol), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 0.5N hydrochloric acid, water and saturated brine in this order, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate and collected by filtration to give the title compound (29.2 g, 72%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 0.5N hydrochloric acid, water and saturated brine in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with hexane/ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-8e1954020a80456c8034af18b5f918f6
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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