Water → HCID 140562199, compound

HRID 2095758Notes

Reaction equation

HRID 2095758 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:13][CH:14]=1.C(N(CC)C(C)C)(C)C.I[CH2:47][C:48]([NH2:50])=[O:49].O>CN(C)C=O>[NH2:50][C:48](=[O:49])[CH2:47][N:11]1[CH:10]=[C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:3][C:2]=2[F:1])[CH:14]=[CH:13]/[C:12]/1=[N:15]/[S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 58158517HCID 58158517, compound

Product 1

HCID 140562199HCID 140562199, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl {3-fluoro-4-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}carbamate (35.0 g, 69.0 mmol) in N,N-dimethylformamide (350 mL) were added N,N-diisopropylethylamine (15.6 mL, 89.6 mmol) and iodoacetamide (16.6 g, 89.6 mmol), and the mixture was stirred at room temperature for 24 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate/tetrahydrofuran. The combined organic layer was washed with water and saturated brine, 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 (28.0 g, 72%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate/tetrahydrofuran
  2. washThe combined organic layer was washed with water and saturated brine
  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-25abf445a9524789bfd70b4c897d0b5d
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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