Hydrochloric Acid → 3-[2-Chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-1,3-dihydro-2H-imidazo-[4,5-b]pyridin-2-one

HRID 1513037Notes

Reaction equation

HRID 1513037 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.[Cl:11][C:12]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:15][C:13]=1[NH2:14].C(=O)([O-])[O-].[K+].[K+].Cl.C[N:40](C)[CH:41]=[O:42]>[Cu]>[Cl:11][C:12]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:15][C:13]=1[N:14]1[C:2]2=[N:10][CH:9]=[CH:8][CH:7]=[C:3]2[NH:40][C:41]1=[O:42]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acidHCID 231200411-(3-Amino-4-chlorobenzenesulfonyl)-1,2,3,4-tetrahydroquinoline

Product 1

HCID 593100753-[2-Chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]-1,3-dihydro-2H-imidazo-[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-chloronicotinic acid (0.13 g) and 2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)aniline (0.3 g) in N,N-dimethylformamide (2 mL) were added copper powder (6 mg) and potassium carbonate (0.13 g), and the mixture was heated at reflux for 8 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in 1,4-dioxane (10 mL) To the solution were added triethylamine (0.42 mL) and diphenylphosphoryl azide (0.26 mL), and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/2) to give the title compound (48 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in 1,4-dioxane (10 mL) To the solution
  8. additionwere added triethylamine (0.42 mL) and diphenylphosphoryl azide (0.26 mL)
  9. additionThe reaction mixture was poured into 1 mol/L hydrochloric acid
  10. extractionthe resulting mixture was extracted with ethyl acetate
  11. washThe extract was washed with water and brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was removed under reduced pressure
  14. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/2)

Sources & evidence

ORD record
ord-632a8fb5b9614275a1cae57a099b1fa6
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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