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HCID 23543228, Verbindung → 8-Butyl-6-oxo-2-(2-methoxyphenyl)-imidazo[1,2-a]pyrazine

HRID 639420
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 639420
C(OC(=O)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[N:8]=[C:7]1[C@@H:19]([NH:24][C:25]([O:27]CC1C=CC=CC=1)=O)[CH2:20][CH2:21][CH2:22][CH3:23])C>CC(O)=O.[Pd]>[CH2:20]([C:19]1[C:7]2[N:6]([CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])[N:8]=2)[CH2:5][C:25](=[O:27])[N:24]=1)[CH2:21][CH2:22][CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 23543228HCID 23543228, Verbindung

Produkt 1

HCID 220168358-Butyl-6-oxo-2-(2-methoxyphenyl)-imidazo[1,2-a]pyrazineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The product from Step 1.d. (compound v where R3 is n-butyl, R4 is 2-methoxyphenyl, and R5 and R6 are H) (11.5 g, 23.9 mmol) was dissolved in HOAc (100 ml) containing 10% Pd on carbon catalyst (500 mg) and hydrogenated under 50 psi of H2 for about 3 hours at room temperature. The catalyst was removed by filtration through a 3 cm pad of diatomaceous earth and the filtrate was warmed at about 70° C. for about 2 hours. The mixture was concentrated to a solid under reduced pressure, dissolved in CH2Cl2 (100 ml) and washed with saturated NaHCO3 solution (125 ml). The CH2Cl2 layer was dried over Na2SO4, filtered and 275 ml hexanes was added. Product was filtered off and dried to constant weight to yield 6.21 g (87%) of product, m.r.=200-202° C., NMR (300 MHz, DMSO-d6, 30° C.) 8.5-8.6 (1H, s), 8.0-8.1 (1H, d), 7.4-7.6 (1H, s), 7.1-7.3 (1H, t), 7.0-7.1 (1H, d), 6.9-7.1 (1H, t), 4.55-4.8 (2H, q), 4.55-4.7 (1H, t), 3.8-4.0 (3H, s), 1.75-1.95 (2H, m), 1.1-1.5 (4H, m), 0.8-0.9 (3H, t).

Aufarbeitung

  1. customThe catalyst was removed by filtration through a 3 cm pad of diatomaceous earth
  2. concentrationThe mixture was concentrated to a solid under reduced pressure
  3. dissolutiondissolved in CH2Cl2 (100 ml)
  4. washwashed with saturated NaHCO3 solution (125 ml)
  5. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  6. filtrationfiltered
  7. addition275 ml hexanes was added
  8. filtrationProduct was filtered off
  9. customdried to constant weight

Quellen und Nachweise

ORD-Eintrag
ord-269366ec823b49df919ebc08c6085805
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691859B2

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