1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine → 6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine

HRID 1007783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007783
[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[H][H]>FC(F)(F)C(O)=O.[Pt]=O>[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1

Komponenten

5

Edukt 2

HCID 120158061-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 120158076,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amineAusbeute 0,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A catalytic amount of platinum oxide was added to a solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine (0.4 g, 1.66 mol)) in trifluoroacetic acid. The reaction mixture was reduced on a Parr apparatus at 50 psi (3.5 Kg/cm2) hydrogen pressure overnight. The reaction mixture was filtered and washed with methanol to remove the catalyst. The filtrate was concentrated under vacuum. The residue was combined with dichloromethane and aqueous sodium bicarbonate was added until the mixture was basic. The dichloromethane layer was separated. The aqueous layer was extracted five times with dichloromethane (100 mL). The dichloromethane extracts were combined, dried over magnesium sulfate and concentrated under vacuum. The resulting residue was recrystallized from toluene to provide 0.34 g of 6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine as a solid, m.p. 220-223° C. Analysis: Calculated for C13H19N5+/4H2O: %C, 62.50%H, 7.87; %N, 28.03; Found: %C, 62.50; %H, 7.72; %N, 27.46.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under vacuum
  5. additionwas added until the mixture
  6. customThe dichloromethane layer was separated
  7. extractionThe aqueous layer was extracted five times with dichloromethane (100 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe resulting residue was recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-4ee194e2d2794acaa4614421fe03f719
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797716B2

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