Dabco → 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 1619711Notes

Reaction equation

HRID 1619711 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][N:8]=1.[Cl:19][C:20]1[C:21]([F:31])=[CH:22][C:23]([F:30])=[C:24]([S:26](Cl)(=[O:28])=[O:27])[CH:25]=1.N12CCN(CC1)CC2>C(#N)C>[Cl:19][C:20]1[C:21]([F:31])=[CH:22][C:23]([F:30])=[C:24]([S:26]([N:6]([CH2:5][C:4]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:3]=2[O:2][CH3:1])[C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]=2)(=[O:28])=[O:27])[CH:25]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 27735275-Chloro-2,4-difluorobenzenesulphonyl chlorideHCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

Product 1

HCID 580422515-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(pyrimidin-4-yl)benzenesulfonamideYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine (Preparation 111, 1.80 g, 7.35 mmol), 5-chloro-2,4-difluorobenzene-1-sulfonyl chloride (1.81 g, 7.35 mmol) and 1,4-diazabicyclo[2.2.2]octane (0.82 g, 7.35 mmol) in acetonitrile (50 mL) were stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between dichloromethane (30 mL) and water (15 mL). The organic layer was separated and dried over anhydrous MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel eluting with 10% dichloromethane in ethyl acetate to give the title compound (1.47 g, 44%) as an orange solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between dichloromethane (30 mL) and water (15 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 10% dichloromethane in ethyl acetate

Sources & evidence

ORD record
ord-48f83373756d49bca92a6e356072bb46
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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