Benzenesulfonamide → HCID 136026947, compound

HRID 1673836Notes

Reaction equation

HRID 1673836 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)=[C:6]([CH2:23][CH2:24][CH3:25])[N:5]=[C:4]([CH3:26])[N:3]=1.[C:27]1([S:33]([NH2:36])(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:37](=[O:40])([O-])[O-:38].[K+].[K+].C[N:44](C)C(=O)C>C(OCC)(=O)C>[CH3:26][C:4]1[N:3]=[C:2]([NH:36][S:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:35])=[O:34])[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:44][C:37](=[O:40])[O:38][N:22]=3)=[CH:11][CH:10]=2)=[C:6]([CH2:23][CH2:24][CH3:25])[N:5]=1

Participants

6

Reactant 4

HCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 10428692HCID 10428692, compound

Product 1

HCID 136026947HCID 136026947, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4′-[(4-chloro-2-methyl-6-propylpyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (0.72 g), benzenesulfonamide (0.63 g) and potassium carbonate (0.55 g) in N,N-dimethylacetamide (10 mL) was stirred at 150° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. A mixture of the residue, hydroxylammonium chloride (1.4 g), sodium hydrogen carbonate (2.0 g) and dimethyl sulfoxide (10 mL) was stirred at 90° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 mL), N,N′-carbonyldiimidazole (0.49 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.45 mL) were added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (0.87 g, 80%) as a white solid.

Workup

  1. washwashed with 5% aqueous potassium hydrogen sulfate solution
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. additionA mixture of the residue, hydroxylammonium chloride (1.4 g), sodium hydrogen carbonate (2.0 g) and dimethyl sulfoxide (10 mL)
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. dissolutionThe residue was dissolved in tetrahydrofuran (10 mL)
  10. additionN,N′-carbonyldiimidazole (0.49 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.45 mL) were added
  11. stirringthe mixture was stirred at room temperature for 30 min
  12. additionThe reaction mixture was diluted with ethyl acetate
  13. washwashed with saturated aqueous potassium hydrogen sulfate solution
  14. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  15. customThe solvent was evaporated under reduced pressure
  16. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-867f9a1c723b404794f6c5d01fca8e39
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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