Water → HCID 23450087, compound

HRID 1839034Notes

Reaction equation

HRID 1839034 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][CH3:22].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>C(Cl)Cl>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][CH3:22])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][S:31]([CH3:30])(=[O:33])=[O:32])[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 10108776HCID 10108776, compound

Product 1

HCID 23450087HCID 23450087, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound of Example 52, 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine (800 mg, 2.67 mmol) in 30 mL of CH2Cl2 was treated with triethylamine (1.10 mL, 8.00 mmol). With vigorous stirring, the solution was treated dropwise with methanesulfonyl chloride (0.217 mL, 2.80 mmol). After 18 h, the reaction was treated with 50 mL of water and the layers were separated. The aqueous portion was extracted with CHCl3 (3×30 mL). The combined organic portions were washed with brine, dried over Na2SO4, filtered and concentrated to yield an off white solid. Purification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH) gave 463 mg of N-{2-[2-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}methanesulfonamide as a white solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous portion was extracted with CHCl3 (3×30 mL)
  3. washThe combined organic portions were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an off white solid
  8. customPurification by column chromatography (SiO2, 95:5:0.5 CHCl3:MeOH:NH4OH)

Sources & evidence

ORD record
ord-1b1e69c5f4ca465e81c5e38f0e0b2268
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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