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Triethylamine → HCID 10181176, compound

HRID 1840845
Notes
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Reaction equation

HRID 1840845 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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-ea87ceee3e95408db1d252694e5085e3
Source dataset
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06683088B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes