Triethylamine → HCID 10181176, compound

HRID 1839009Notes

Reaction equation

HRID 1839009 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[NH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]1[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[C:19]([NH2:28])[C:18]=2[N:17]=[C:16]1[CH2:29][CH2:30][CH2:31][CH3:32].C(N(CC)CC)C.N12CCCN=C1CCCCC2>ClCCl>[CH2:29]([C:16]1[N:15]([CH2:14][CH2:13][O:12][CH2:11][CH2:10][N:9]2[CH2:2][CH2:3][CH2:4][S:5]2(=[O:7])=[O:6])[C:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[C:19]([NH2:28])[C:18]=2[N:17]=1)[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 218980271-[2-(2-Aminoethoxy)ethyl]-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10181176HCID 10181176, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, chloropropylsulfonyl chloride (0.05 ml, 0.46 mmol) was added dropwise to a solution of 1-[2-(2-aminoethoxy)ethyl]-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (0.12 g, 0.37 mmol) and triethylamine (0.065 ml, 0.46 mmol) in dichloromethane (5 ml). The reaction was stirred for 20 hours followed by removal of the solvent in vacuo. The resulting off-white solid was dissolved in N,N-dimethylformamide (5 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.087 ml, 0.58 mmol) was added. The reaction was stirred for 18 hours under an atmosphere of nitrogen and then quenched with water and extracted with dichloromethane (2×). The organic fractions were combined, washed with water followed by brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide an off-white solid. Recrystallization from ethyl acetate yielded 0.068 g of 2-butyl-1-{2-[2-(1,1-dioxidoisothiazolidin-2-yl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine as off-white crystals, m.p. 152-154° C.

Workup

  1. customfollowed by removal of the solvent in vacuo
  2. dissolutionThe resulting off-white solid was dissolved in N,N-dimethylformamide (5 mL)
  3. stirringThe reaction was stirred for 18 hours under an atmosphere of nitrogen
  4. customquenched with water
  5. extractionextracted with dichloromethane (2×)
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide an off-white solid
  11. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-c4c410958410421497f62260231caddd
Source dataset
uspto-grants-2004_01
Patent number
US06677347B2

Reaction notes

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