4-Toluenesulfonyl chloride → HCID 16742453, compound

HRID 2192233Notes

Reaction equation

HRID 2192233 reaction equation
[NH:1]1[C:13]2[C:12]3[N:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.ClC1C=[C:17](C=CC=1)[C:18]([O:20]O)=O.[OH-].[NH4+:26].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30](S(Cl)(=O)=O)=[CH:29][CH:28]=1>ClC(Cl)C.O>[CH2:37]([N:1]1[C:13]2[C:12]3[N:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[C:5]([NH2:26])[C:4]=2[N:3]=[C:2]1[O:20][CH2:18][CH3:17])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 1784207351h-Imidazo[4,5-c][1,5]naphthyridine

Product 1

HCID 16742453HCID 16742453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of 1H-imidazo[4,5-c][1,5]naphthyridine (4.5 g, 14.8 mmol) in dichloroethane (100 mL) was added 3-chloroperoxybenzoic acid (mCPBA) (77%, 4.9 g, 22.2 mmol), and the reaction was stirred at room temperature for 2 hours. To the reaction was then added ammonium hydroxide (100 mL) followed by p-toluenesulfonyl chloride (3.4 g, 17.7 mmol), and the reaction was stirred for 5 days at room temperature. To the reaction was added water and the reaction was transferred to a separatory funnel. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, dried (MgSO4), filtered, and evaporated to afford an orange solid. The product was purified by preparative HPLC (Analogix Separation System, and eluted with a gradient of 0-10% methanol in dichloromethane with 1% ammonium hydroxide) to provide a solid which was triturated with acetonitrile and filtered. The residue was washed with acetonitrile and then with ether and dried in a vacuum oven to afford 1-benzyl-2-ethoxy-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (2.0 g) as a white solid.

Workup

  1. stirringthe reaction was stirred for 5 days at room temperature
  2. customthe reaction was transferred to a separatory funnel
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford an orange solid
  9. customThe product was purified by preparative HPLC (
  10. customAnalogix Separation System
  11. washeluted with a gradient of 0-10% methanol in dichloromethane with 1% ammonium hydroxide)
  12. customto provide a solid which
  13. customwas triturated with acetonitrile
  14. filtrationfiltered
  15. washThe residue was washed with acetonitrile
  16. dry with materialwith ether and dried in a vacuum oven

Sources & evidence

ORD record
ord-278476987f6749039220b6c7ffc51714
Source dataset
uspto-grants-2012_12
Patent number
US08329721B2

Reaction notes

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