N-bromobutanimide → N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,5-difluorobenzenesulfonamide

HRID 239242Notes

Reaction equation

HRID 239242 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](/[C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)\O)[CH:5]=[CH:4][N:3]=1.C1C(=O)N(Br)C(=O)C1.[CH3:37][C:38]([CH3:43])([CH3:42])[C:39](=[S:41])[NH2:40]>CC(N(C)C)=O.CCOC(C)=O.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:41][C:39]([C:38]([CH3:43])([CH3:42])[CH3:37])=[N:40][C:9]=2[C:11]2[CH:12]=[C:13]([NH:17][S:18]([C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[F:28])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 67184N-bromobutanimideHCID 30311302,2-DimethylpropanethioamideHCID 136088569N-{3-[(Z)-2-(2-Chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamide

Product 1

HCID 57989961N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,5-difluorobenzenesulfonamideYield 82.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-{3-[(Z)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamide (1.0 g, 2.4 mmol) in 25 mL DMA, NBS (0.420 g, 2.4 mmol) was added and the solution was allowed to stir 15 minutes at rt. 2,2-Dimethylpropanethioamide (0.277 g, 2.359 mmol) was then added and the reaction mixture was heated at 80° C. for 2 h. The reaction mixture was diluted with EtOAc and washed with water×3. The organic layer was dried over MgSO4 and filtered. The organic solution was evaporated onto silica gel and chromatographed. 0-50% EtOAc in DCM to give the title compound (1.01 g, 81% yield). ES-LCMS m/z 521.1 (M+H).

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 2 h
  2. washwashed with water×3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customThe organic solution was evaporated onto silica gel
  6. customchromatographed

Sources & evidence

ORD record
ord-dd5a0eddcf764853bc4a4aefe14761f6
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

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