Cesium carbonate → HCID 11495716, compound

HRID 1786135Notes

Reaction equation

HRID 1786135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:29][C:30]([N:32]([CH3:34])[CH3:33])=[O:31]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH2:29][C:30]([N:32]([CH3:34])[CH3:33])=[O:31])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 11508472HCID 11508472, compound

Product 1

HCID 11495716HCID 11495716, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dichloro-N-(2-isopropyl-pyrimidin-4-yl)-benzenesulfonamide (80 mg, example 14) was dissolved in DMF (1 mL) and treated with cesium carbonate (113 mg). To the mixture was added 2-chloro-N,N-dimethylacetamide (37 mg) and the resulting suspension was allowed to stir at room temperature for 48 hours and then at 80° C. for 24 hours. The mixture was diluted with ethyl acetate, washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography on silica gel using DCM/MeOH/NH4OH 9:1:0.1 as an eluant. The desired product was obtained as a colorless glass (28 mg). MS (ESI): 431.3 (MH+).

Workup

  1. waitat 80° C. for 24 hours
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-38e55c372faf4483810a64036efa482b
Source dataset
uspto-grants-2009_03
Patent number
US07507733B2

Reaction notes

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