Triethylamine → HCID 10294835, compound

HRID 1840833Notes

Reaction equation

HRID 1840833 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][CH2:22][O:23][CH3:24].CCN(CC)CC.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl.CO.CCOCC>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][CH2:22][O: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 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 121062041-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10294835HCID 10294835, compoundYield 41.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-[2-(2-Aminoethoxy)ethyl]-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine (750 mg, 2.28 mmol) was dissolved in 30 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. To the stirred solution were added Et3N (0.64 mL, 4.56 mmol) and methanesulfonyl chloride (176 μL, 2.28 mmol) and the reaction was allowed to warm to room temperature over 2 h. The reaction mixture was then quenched by addition of saturated NaHCO3 solution (30 mL). The organic layer was separated and washed with H2O (3×25 mL) and brine, dried over Na2SO4 and concentrated under reduced pressure to give a tan foam. The foam was dissolved in a minimum amount of MeOH and Et2O was added and a solid percipitated from the solution. The off-white solid was isolated by filtration and dried to yield 385 mg of N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)methanesulfonamide. m.p. 114.0-117.0° C.;

Workup

  1. temperatureto warm to room temperature over 2 h
  2. customThe reaction mixture was then quenched by addition of saturated NaHCO3 solution (30 mL)
  3. customThe organic layer was separated
  4. washwashed with H2O (3×25 mL) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a tan foam
  8. additionwas added
  9. customThe off-white solid was isolated by filtration
  10. customdried

Sources & evidence

ORD record
ord-fc245b36499948e0ad298a50214be975
Source dataset
uspto-grants-2004_01
Patent number
US06683088B2

Reaction notes

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