2-Propanesulfonyl chloride → HCID 23450085, compound

HRID 1839033Notes

Reaction equation

HRID 1839033 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[CH3:21].[CH:22]([S:25](Cl)(=[O:27])=[O:26])([CH3:24])[CH3:23]>N1C=CC=CC=1>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH3:21])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][S:25]([CH:22]([CH3:24])[CH3:23])(=[O:27])=[O:26])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 10401692HCID 10401692, compound

Product 1

HCID 23450085HCID 23450085, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the compound of Example 51, 1-[2-(2-aminoethoxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.00 g, 3.50 mmol) in 30 mL of pyridine was chilled in an ice water bath. The stirred solution was treated dropwise with isopropylsulfonyl chloride (0.39 mL, 3.50 mmol) and the reaction was allowed to gradually warm to room temperature. After 18 h, the reaction was concentrated. The crude product was purified by column chromatography (SiO2, 90:10:0.5 CHCl3:MeOH:NH4OH) and then triturated in hexanes to give 314 mg of N-{2-[2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}propane-2-sulfonamide as a white solid.

Workup

  1. concentrationthe reaction was concentrated
  2. customThe crude product was purified by column chromatography (SiO2, 90:10:0.5 CHCl3:MeOH:NH4OH)
  3. customtriturated in hexanes

Sources & evidence

ORD record
ord-2708c8d6b7cc41f5ba727801d80649d0
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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