Triethylamine → HCID 9843452, compound

HRID 1839086Notes

Reaction equation

HRID 1839086 reaction equation
[NH2:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[C:5]1[CH2:18][O:19][CH2:20][CH3:21].CCN(CC)CC.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[NH2:17][C:8]1[C:7]2[N:6]=[C:5]([CH2:18][O:19][CH2:20][CH3:21])[N:4]([CH2:3][C:2]([NH:1][S:32]([CH3:31])(=[O:34])=[O:33])([CH3:22])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10380870TLR7/8 agonist 3

Product 1

HCID 9843452HCID 9843452, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-Amino-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline-4-amine (111 mg, 0.355 mmol) was dissolved in 5 mL of anhydrous CH2Cl2 and cooled to 0° C. under N2. To the stirred solution were added Et3N (99 μL, 0.71 mmol) and methanesulfonyl chloride (28 μL, 0.36 mmol) and the reaction was allowed to warm to ambient temperature overnight. The reaction mixture was then quenched by addition of saturated NaHCO3 solution (5 mL). The organic layer was separated and washed with H2O (2×5 mL) and brine, dried over Na2SO4 and concentrated under reduced pressure to give a tan foam. Purification by column chromatography (SiO2, 2.5%-5% MeOH/CHCl3) gave N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (75 mg) as a white foam.

Workup

  1. temperatureto warm to ambient temperature overnight
  2. customThe reaction mixture was then quenched by addition of saturated NaHCO3 solution (5 mL)
  3. customThe organic layer was separated
  4. washwashed with H2O (2×5 mL) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give a tan foam
  8. customPurification by column chromatography (SiO2, 2.5%-5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-e824d57c64494ba1a87758458eb1bb52
Source dataset
uspto-grants-2004_01
Patent number
US06677349B1

Reaction notes

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