Tetrahydrofuran → 1-{3-[4-amino-8-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one

HRID 244871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244871
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][CH2:25][O:26][CH3:27])[N:14]([CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[C:10]=2[C:9]2[CH:8]=[C:7]([CH2:28][CH2:29][N:30]3C(=O)C4C(=CC=CC=4)C3=O)[CH:6]=[CH:5][C:4]=2[N:3]=1.O1CCCC1.O.NN>C(O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][CH2:25][O:26][CH3:27])[N:14]([CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[C:10]=2[C:9]2[CH:8]=[C:7]([CH2:28][CH2:29][NH2:30])[CH:6]=[CH:5][C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)2×HCID 690766432-(2-{4-amino-2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)dione

Produkt 1

HCID 576572621-{3-[4-amino-8-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-oneAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-(2-{4-Amino-2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)dione (2.2 g, 4.1 mmol) was dissolved in 2:1 ethanol:tetrahydrofuran (40 mL), combined with hydrazine hydrate (410 mg, 8.2 mmol) and heated at reflux temperature for three hours. Additional hydrazine hydrate (0.25 mL) was added and the solution was refluxed for an additional 1.5 hours. The reaction was cooled to ambient temperature, filtered and the filtrate concentrated under reduce pressure. Purification by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-40% CMA:chloroform gradient over 3.8 L) provided 650 mg of 1-{3-[4-amino-8-(2-aminoethyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one as an off-white solid. MS (ESI) m/z 411 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux temperature for three hours
  3. temperaturethe solution was refluxed for an additional 1.5 hours
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customPurification by chromatography
  7. washeluting with a 0-40% CMA

Quellen und Nachweise

ORD-Eintrag
ord-c764cff3d85940a1b48fac4dbf64836d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658666B2

Notizen zur Reaktion

Wird geladen…