Water → HCID 21099510, compound

HRID 2377019Notes

Reaction equation

HRID 2377019 reaction equation
[C:1]([NH:4][OH:5])(=O)[CH3:2].CC(C)([O-])C.[K+].F[C:13]1[CH:20]=[CH:19]C=[C:17]([S:21]([C:24]2[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:14]=1C#N.O.C[N:41](C)C=O>>[F:38][C:35]1[CH:34]=[CH:33][C:32](/[CH:31]=[CH:30]/[C:27]2[CH:28]=[CH:29][C:24]([S:21]([C:17]3[C:2]4[C:1]([NH2:41])=[N:4][O:5][C:19]=4[CH:20]=[CH:13][CH:14]=3)(=[O:22])=[O:23])=[CH:25][CH:26]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1990Acetohydroxamic AcidHCID 6228DimethylformamideHCID 21099476HCID 21099476, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21099510HCID 21099510, compoundYield 29%

Procedure

A solution of acetohydroxamic acid (75 mg, 1 mmol) in N,N-dimethylformamide was treated at room temperature with potassium tert-butoxide and stirred for 30 minutes. 2-fluoro-6-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)benzonitrile (Example 112, 100 mg, 0.26 mmol) was added and the reaction stirred for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine (×5), dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica to give the title compound (30 mg, 29%).

Workup

  1. stirringthe reaction stirred for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine (×5)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-b60ecf76584641838326e64a5287b166
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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