3-(1,3,2-Dioxaborinan-2-yl)pyridine → 2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1818164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818164
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([CH2:16][C:17]([O:20][CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])([CH3:19])[CH3:18])[C:14]([CH2:27][O:28][CH2:29][CH3:30])=[N:13][C:7]=3[C:8]([NH2:12])=[N:9][C:10]=2[CH:11]=1.B1([C:37]2[CH:42]=[CH:41][CH:40]=[N:39][CH:38]=2)OCCCO1>>[CH2:29]([O:28][CH2:27][C:14]1[N:15]([CH2:16][C:17]([O:20][CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])([CH3:19])[CH3:18])[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([C:37]4[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:12])[C:7]=2[N:13]=1)[CH3:30]

Komponenten

3

Edukt 2

HCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 219844257-Bromo-2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinolin-4-amine

Produkt 1

HCID 219843222-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amineAusbeute 58,6 %

Versuchsvorschrift

7-Bromo-2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinolin-4-amine (1.2 g, 2.4 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (0.47 g, 2.9 mmol) were coupled according to the method described in Part J of Example 1. The work-up procedure used in Part F of Examples 125-135 was followed. The crude product was purified by column chromatography on silica gel (eluting sequentially with 95:5 and 90:10 dichloromethane:methanol) followed by recrystallization from acetonitrile (52 mL/g). The crystals were isolated by filtration, washed with acetonitrile, and dried for four hours under vacuum at 65° C. to provide 0.70 g of 2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as white, crystalline plates, mp 202-204° C.

Aufarbeitung

  1. customThe crude product was purified by column chromatography on silica gel (
  2. washeluting sequentially with 95:5 and 90:10 dichloromethane
  3. custommethanol) followed by recrystallization from acetonitrile (52 mL/g)
  4. customThe crystals were isolated by filtration
  5. washwashed with acetonitrile
  6. customdried for four hours under vacuum at 65° C.

Quellen und Nachweise

ORD-Eintrag
ord-295d14a620594aca9043ba1a3d42969e
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

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