4-Toluenesulfonyl chloride → tert-butyl 2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate

HRID 719217Notes

Reaction equation

HRID 719217 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[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.[NH4+:32].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCCl>[NH2:32][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[N:6]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium Hydroxide2×HCID 12106202Tert-butyl-2-{2-[2-(2-methoxyethyl)-5-oxido-1h-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate

Product 1

HCID 12106203tert-butyl 2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of tert-butyl 2-{2-[2-(2-methoxyethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy)ethylcarbamate (10.6 g, 24.6 mmol) in 100 mL of 1,2-dichloroethane was heated to 60° C. and treated with 10 mL of concentrated NH4OH solution. To the rapidly stirred solution was added solid p-toluenesulfonyl chloride (7.05 g, 37.0 mmol) over a 10 min period. The reaction mixture was treated with an additional 1 mL concentrated NH4OH solution and then sealed in a pressure vessel and heating was continued for 2 h. The reaction mixture was then cooled and treated with 100 mL of CHCl13. The reaction mixture was then washed with H2O, 1% Na2CO3 solution (2×) and brine. The organic portion was dried over Na2SO4 and concentrated to give 10.6 g of tert-butyl 2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate as a brown foam.

Workup

  1. customsealed in a pressure vessel
  2. temperatureheating
  3. temperatureThe reaction mixture was then cooled
  4. additiontreated with 100 mL of CHCl13
  5. washThe reaction mixture was then washed with H2O, 1% Na2CO3 solution (2×) and brine
  6. dry with materialThe organic portion was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-078637a0d44d49aa9242a6a821ccfb89
Source dataset
uspto-grants-2006_11
Patent number
US07132429B2

Reaction notes

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