Reaktion #9507

ord-f18f803e88054fb58ebacb523833a126

Reaktionsgleichung

Nc1cnc2cc(-c3ccccc3)ccc2c1NCCCN1CCCC1=O
1-[3-(3-Amino-7-phenylquinolin-4-ylamino)propyl]pyrrolidin-2-one
CCOCC(=O)Cl
ethoxyacetyl chloride
CCN(CC)CC
Triethylamine
CCOCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCN1CCCC1=O
1-[3-(2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]pyrrolidin-2-one
Ausbeute 56.7%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe product from Part D was purified by column chromatography on silica gel (
  2. 2
    Wascheneluting with acetone

Vorschrift

1-[3-(3-Amino-7-phenylquinolin-4-ylamino)propyl]pyrrolidin-2-one (2.21 g, 6.13 mmol) was treated with ethoxyacetyl chloride (0.95 mL, 8.76 mmol) according to the methods described in Parts C and D of Examples 152–156. Triethylamine (8.6 mmol) was added in Part C. The product from Part D was purified by column chromatography on silica gel (eluting with acetone and then chloroform:methanol in a gradient from 95:5 to 90:10) to provide 1.49 g of 1-[3-(2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]pyrrolidin-2-one as a brown solid.

Quelle

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