Potassium Iodide → 2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride

HRID 1818177

Reaktionsgleichung

Reaktionsgleichung von HRID 1818177
[NH2:1][C:2]([NH2:4])=[S:3].[I-].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][Cl:26])[C:19]([CH2:27][O:28][CH2:29][CH3:30])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1>CN(C=O)C>[ClH:26].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][S:3][C:2](=[NH:4])[NH2:1])[C:19]([CH2:27][O:28][CH2:29][CH3:30])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 2723790ThioureaHCID 219843917-bromo-1-(5-chloropentyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

Produkt 1

HCID 219844052-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochlorideAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Thiourea (0.29 g, 3.8 mmol) and potassium iodide (0.052 g, 3.1 mmol) were sequentially added to a suspension of 7-bromo-1-(5-chloropentyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (1.3 g, 3.2 mmol) in DMF (15 mL), and the reaction was heated at 110° C. for 24 hours. The DMF was removed under reduced pressure, and the residue was partitioned between saturated aqueous sodium bicarbonate (40 mL) and dichloromethane (50 mL). The mixture was adjusted to pH 7 with the addition of 10% hydrochloric acid. Product remained on the walls of the reaction flask and was dissolved with methanol. The resulting solution was concentrated under reduced pressure to provide a solid. The aqueous layer was concentrated under reduced pressure, and the resulting solid was triturated with methanol and isolated by filtration. The filtrate was concentrated under reduced pressure, and the residue was triturated and isolated as described above. The isolated solids were combined and dried under high vacuum to provide 1.49 g of 2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride as a yellow solid.

Aufarbeitung

  1. customThe DMF was removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate (40 mL) and dichloromethane (50 mL)
  3. additionThe mixture was adjusted to pH 7 with the addition of 10% hydrochloric acid
  4. dissolutionwas dissolved with methanol
  5. concentrationThe resulting solution was concentrated under reduced pressure
  6. customto provide a solid
  7. concentrationThe aqueous layer was concentrated under reduced pressure
  8. customthe resulting solid was triturated with methanol
  9. customisolated by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was triturated
  12. customisolated
  13. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d7f29f37cfd348b6bef148acd738922a
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

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