Water → HCID 21936592, compound

HRID 1839022Notes

Reaction equation

HRID 1839022 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N+:7]([O-])=[CH:6][C:5]=2[N:15]=1.[NH4+:29].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl>[NH2:29][C:6]1[C:5]2[N:15]=[C:2]([CH3:1])[N:3]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:4]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 21936588HCID 21936588, compound

Product 1

HCID 21936592HCID 21936592, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 2-[2-(2-methyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (11.21 g, 29.0 mmol) in 75 mL of CH2Cl2 was treated with 75 mL of concentrated NH4OH solution. The mixture was chilled in an ice water bath. To the rapidly stirred mixture was added solid p-toluenesulfonyl chloride (5.53 g, 29.0 mmol) over a 10 min period. The reaction mixture was then warmed to room temperature and treated with 75 mL of CH2Cl2 and 75 mL of water. The organic portion was then washed with 1% Na2CO3 solution (3×) and brine. The organic portion was dried over Na2SO4 and concentrated and triturated in ether to yield 7.13 g of tert-butyl 2-[2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as a light green solid.

Workup

  1. temperatureThe mixture was chilled in an ice water bath
  2. washThe organic portion was then washed with 1% Na2CO3 solution (3×) and brine
  3. dry with materialThe organic portion was dried over Na2SO4
  4. concentrationconcentrated
  5. customtriturated in ether

Sources & evidence

ORD record
ord-e5bad1d69a384c21aaf049718694d084
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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