4-Toluenesulfonyl chloride → HCID 86596851, compound

HRID 1373933Notes

Reaction equation

HRID 1373933 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:18]=1)[CH3:2].[NH4+:31].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.O>[NH2:31][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([NH:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 86594227HCID 86594227, compound

Product 1

HCID 86596851HCID 86596851, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of tert-butyl {3-[(2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.39 g, 3.35 mmol) in 35 mL of CHCl3 was treated with 15 mL of concentrated NH4OH solution and p-toluenesulfonyl chloride (0.67 g, 3.51 mmol). After 15 min, the reaction mixture was diluted with water and CHCl3 and the phases were separated. The organic portion was washed with 10% Na2CO3 solution and water. The combined aqueous washes were back-extracted with CHCl3. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl {3-[(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}carbamate (1.30 g) as an orange foam.

Workup

  1. customthe phases were separated
  2. washThe organic portion was washed with 10% Na2CO3 solution and water
  3. extractionThe combined aqueous washes were back-extracted with CHCl3
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98b5ea60c44c4758bd3f231e3f96d7b0
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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