Water → HCID 23450083, compound

HRID 1839036Notes

Reaction equation

HRID 1839036 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][O:22][CH2:23][CH3:24].C(N(CC)CC)C.[CH:32]([S:35](Cl)(=[O:37])=[O:36])([CH3:34])[CH3:33].O>C(Cl)Cl>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][O:22][CH2:23][CH3:24])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][S:35]([CH:32]([CH3:34])[CH3:33])(=[O:37])=[O:36])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 10359216HCID 10359216, compound

Product 1

HCID 23450083HCID 23450083, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the compound of Example 53, 1-[2-(2-aminoethoxy)ethyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (980 mg, 2.98 mmol) in 20 mL CH2Cl2 was treated with triethylamine (1.04 mL, 7.45 mmol) and chilled in an ice water bath. With vigorous stirring, the solution was treated dropwise with isopropylsulfonyl chloride (0.351 mL, 3.13 mmol). After 18 h, the reaction was treated with 25 mL CH2Cl2 and 25 mL water and the layers were separated. The organic portion was washed with 1% Na2CO3 solution, water, brine, dried over Na2SO4, filtered and concentrated to yield a yellow foam. Purification by column chromatography (SiO2, 90:10:0.5 CHCl3:MeOH:NH4OH) followed by recrystallization from CH2Cl2/hexanes gave 308 mg of N-(2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)propane-2-sulfonamide as a light yellow solid.

Workup

  1. temperaturechilled in an ice water bath
  2. customthe layers were separated
  3. washThe organic portion was washed with 1% Na2CO3 solution, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow foam
  8. customPurification by column chromatography (SiO2, 90:10:0.5 CHCl3:MeOH:NH4OH)
  9. customfollowed by recrystallization from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-29d3430fd3dc463d9c11bf4cffe6d28b
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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