Ethoxyacetyl chloride → 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}tetrahydro-2H-pyran-4-ol

Reaktionsgleichung

[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]1([OH:20])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:21]([O:23][CH2:24][C:25](Cl)=O)[CH3:22]>>[CH2:21]([O:23][CH2:24][C:25]1[N:12]([CH2:13][C:14]2([OH:20])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:22]

Komponenten

Edukt 2

HCID 84189Ethoxyacetyl chloride

HCID 574578244-[(3-Aminoquinolin-4-ylamino)methyl]tetrahydropyran-4-ol

Produkt 1

HCID 575153964-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}tetrahydro-2H-pyran-4-olAusbeute 80,2 %

Versuchsvorschrift

4-{[(3-Aminoquinolin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol (7.50 g, 27.4 mmol) was reacted with ethoxyacetyl chloride (3.70 g, 30.1 mmol) and the resulting product was cyclized according to the method described in Part E of Example 9 to provide 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}tetrahydro-2H-pyran-4-ol as pale tan crystals (7.50 g, 76%) after crystallization from ethanol.

Quellen und Nachweise

ORD-Eintrag: ord-0d76c944072443cbbdca7e2d326b6acd
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541438B2

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