Isopropyl isocyanate → N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N'-(1-methylethyl)urea

HRID 9437

Reaktionsgleichung

Reaktionsgleichung von HRID 9437
[NH2:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:23])[C:7]=2[N:6]=[C:5]1[CH2:24][O:25][CH2:26][CH3:27].[CH:28]([N:31]=[C:32]=[O:33])([CH3:30])[CH3:29]>C(Cl)(Cl)Cl>[NH2:23][C:8]1[C:7]2[N:6]=[C:5]([CH2:24][O:25][CH2:26][CH3:27])[N:4]([CH2:3][CH2:2][NH:1][C:32]([NH:31][CH:28]([CH3:30])[CH3:29])=[O:33])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][C:10]=2[N:9]=1

Komponenten

4

Edukt 2

HCID 61277Isopropyl isocyanateHCID 219841051-(2-Aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 21984297N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N'-(1-methylethyl)ureaAusbeute 28,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 1-(2-aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (2.50 g, 6.90 mmol) in chloroform (50 mL) was treated with isopropyl isocyanate (0.65 mL, 6.9 mmol) according to the method described in Examples 377–379. The crude product was purified by column chromatography on silica gel (eluting with 94:6 chloroform:methanol) followed by trituration with acetonitrile (15 mL/g) at 95° C. The mixture was cooled in an ice bath, isolated by filtration, and dried for one hour in a vacuum oven at 100° C. to provide 0.88 g of N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N′-(1-methylethyl)urea as a white solid, mp 194–196° C.

Aufarbeitung

  1. customThe crude product was purified by column chromatography on silica gel (eluting with 94:6 chloroform:methanol)
  2. customfollowed by trituration with acetonitrile (15 mL/g) at 95° C
  3. temperatureThe mixture was cooled in an ice bath
  4. customisolated by filtration
  5. customdried for one hour in a vacuum oven at 100° C.

Quellen und Nachweise

ORD-Eintrag
ord-d16d8d902d0c45cfb7ea9fa85a26dbda
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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