Water → HCID 70794439, compound

HRID 2095753Notes

Reaction equation

HRID 2095753 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[N:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.I[CH2:46][C:47]([NH2:49])=[O:48].O>CN(C)C=O>[NH2:49][C:47](=[O:48])[CH2:46][N:17]1[C:12](=[N:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:21][CH:20]=2)=[CH:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 58158575HCID 58158575, compound

Product 1

HCID 70794439HCID 70794439, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl {4-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}carbamate (23.8 g, 48.6 mmol) in N,N-dimethylformamide (238 mL) were added N,N-diisopropylethylamine (11.0 mL, 63.2 mmol) and iodoacetamide (11.7 g, 63.2 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 (20.6 g, 78%).

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-ce98e15a30124435a24525c9cada9300
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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