(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amine → 6-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

HRID 2383145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2383145
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:19]([O-])=O)=[C:12]2[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=C2C(C(NCCOC3C=CC=CC=3)=C([N+]([O-])=O)C=N2)=CC=1)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([NH2:19])=[C:12]2[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 67050949(7-Benzyloxy-3-nitroquinolin-4-yl)-(2-phenoxyethyl)amineHCID 670510536-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine

Produkt 1

HCID 670509646-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine

Versuchsvorschrift

A modification of the general method described in Part B of Example 46 was followed using 6-benzyloxy-N-[5-(methylthio)pentyl]-3-nitroquinolin-4-amine (5.1 g, 12 mmol) in lieu of (7-benzyloxy-3-nitro-quinolin-4-yl)-(2-phenoxyethyl)amine. The reaction was maintained under hydrogen pressure (49 psi, 3.4×105 Pa) for three hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with methanol (100 mL) and chloroform (50 mL). The filtrate was concentrated under reduced pressure to provide 6-benzyloxy-N4-[5-(methylthio)pentyl]quinoline-3,4-diamine as a yellow oil, which was used without purification.

Aufarbeitung

  1. temperatureThe reaction was maintained under hydrogen pressure (49 psi, 3.4×105 Pa) for three hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with methanol (100 mL) and chloroform (50 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b29e1d09064d43d3b3543c74f0f4ee58
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263594B2

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