Reaktion #9531

ord-300f431f77bb4ac1863898c99805673a

Reaktionsgleichung

CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN
1-(2-Aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine
CCN(CC)CC
triethylamine
CC(C)C(=O)Cl
isobutyryl chloride
CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)C(C)C
N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-2-methylpropanamide
Ausbeute 32.8%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude product was recrystallized from 93:7 acetonitrile
  2. 2
    Trocknenwater and then from isopropanol (7.3 mL/g) and dried for two hours in a drying oven

Vorschrift

1-(2-Aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.50 mmol) was treated with triethylamine (1.00 mL, 7.20 mmol) and isobutyryl chloride (0.64 mL, 6.10 mmol) according to the method described in Part B of Examples 372–376. The crude product was recrystallized from 93:7 acetonitrile:water and then from isopropanol (7.3 mL/g) and dried for two hours in a drying oven to provide 0.78 g of N-{2-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-2-methylpropanamide as a white solid, mp 213–215° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091214B2uspto-grants-2006_08