Water → HCID 23450088, compound

HRID 1839032Notes

Reaction equation

HRID 1839032 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].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>CN1CCCC1=O>[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:30]([CH3:29])(=[O:32])=[O:31])[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 31297Methanesulfonyl chlorideHCID 10401692HCID 10401692, compound

Product 1

HCID 23450088HCID 23450088, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of the compound of Example 51, 1-[2-(2-aminoethoxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.570 g, 5.50 mmol) in 40 mL of 1-methyl-2-pyrrolidinone was treated with triethylamine (1.53 mL, 11.0 mmol). With vigorous stirring, methanesulfonyl chloride (0.426 mL, 5.50 mmol) was added dropwise. After 18 h, the reaction was treated with 50 mL of water and then concentrated to yield a solid. The solid was purified by column chromatography (SiO2, 90:10:0.5 CHCl3:MeOH:NH4OH) to yield 244 mg of N-{2-[2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}methanesulfonamide as a white solid.

Workup

  1. concentrationconcentrated
  2. customto yield a solid
  3. customThe solid was purified by column chromatography (SiO2, 90:10:0.5 CHCl3:MeOH:NH4OH)

Sources & evidence

ORD record
ord-ed29933e3eb5436988641e3c3d75fe9e
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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