Toluene → N1-[3-(1H-imidazo[4,5-c]quinolin-1-yl)propyl]benzamide

HRID 746508

Reaktionsgleichung

Reaktionsgleichung von HRID 746508
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[C:27]1(C)C=CC=CC=1.C(OC(OCC)OCC)C>C(O)(C)C.[Pt]>[N:14]1([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:1]=[CH:27]1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 31214Ethyl orthoformateHCID 23512704N1-{3-[(3-nitroquinolin-4-yl)amino]propyl}benzamide

Produkt 1

HCID 23512712N1-[3-(1H-imidazo[4,5-c]quinolin-1-yl)propyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A suspension of N1-{3-[(3-nitroquinolin-4-yl)amino]propyl}benzamide (1.0 g, 2.8 mmol) in isopropyl alcohol (120 mL) was warmed to dissolve some of the material. A catalytic amount of platinum on carbon was added and the reaction mixture was placed under a hydrogen atmosphere at 50 psi (3.4×104 pascals) on a Parr apparatus. After 3 hours the reaction mixture was filtered to remove catalyst. The filtrate was concentrated under vacuum to provide crude N1-{3-[(3-aminoquinolin-4-yl)amino]propyl}benzamide as an oil. Toluene (100 mL) was added to the oil followed by the addition of triethylorthoformate (0.8 g, 5.6 mmol). The reaction mixture was heated on a steam bath overnight. The reaction mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration to provide 0.53 g of N1-[3-(1H-imidazo[4,5-c]quinolin-1-yl)propyl]benzamide as an off white solid, m.p. 188-190° C. 1H NMR (500 MHz, DMSO-d6) δ 8.67 (t, J=5.5 Hz, 1H), 8.50 (s, 1H), 8.37 (d, J=7.5 Hz, 1H), 8.17 (dd, J=8.0, 1.5 Hz, 11H), 7.87 (d, J=7.0 Hz, 2H), 7.71 (dt, J=7.5, 1.5 Hz, 11H), 7.56 (dt, J=7.5, 1.0 Hz, 1H), 7.54 (d, J=8.0 Hz, 2H), 7.48 (t, J=7.0 Hz, 2H), 4.78 (t, J=7.0 Hz, 2H), 3.38 (q, J=6.0 Hz, 2H), 2.18 (quintet, J=7.0 Hz, 2H).

Aufarbeitung

  1. temperaturewas warmed
  2. dissolutionto dissolve some of the material
  3. filtrationAfter 3 hours the reaction mixture was filtered
  4. customto remove catalyst
  5. concentrationThe filtrate was concentrated under vacuum
  6. customto provide crude N1-{3-[(3-aminoquinolin-4-yl)amino]propyl}benzamide as an oil
  7. temperatureThe reaction mixture was heated on a steam bath overnight
  8. customThe resulting precipitate was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-60e65896e3da463797179315340d4253
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393859B2

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