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Triethylamine → HCID 10181176, Verbindung

HRID 719230
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 719230
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]
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Komponenten

6

Edukt 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

Produkt 1

HCID 10181176HCID 10181176, VerbindungAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2ef8ec60ef274f0ca0348e08db3ed753
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07132429B2

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