Chloroform → HCID 23450089, compound

HRID 1839035Notes

Reaction equation

HRID 1839035 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.[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(Cl)(Cl)Cl>C(Cl)Cl.O>[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:33]([CH3:32])(=[O:35])=[O:34])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10359216HCID 10359216, compound

Product 1

HCID 23450089HCID 23450089, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 of 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 methanesulfonyl chloride (0.242 mL, 3.13 mmol). After 18 h, the reaction was treated with 40 mL CH2Cl2, 20 mL CHCl3, 25 mL water and the layers were separated. The organic portion was washed with 1% Na2CO3 solution, water and brine. The organic portion was then 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 gave 282 mg of N-(2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)methanesulfonamide as light yellow crystals.

Workup

  1. temperaturechilled in an ice water bath
  2. customthe layers were separated
  3. washThe organic portion was washed with 1% Na2CO3 solution, water and brine
  4. dry with materialThe organic portion was then dried 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

Sources & evidence

ORD record
ord-f4907f7006254c44bb53d2b51cf0a9cc
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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