Acetyl chloride → (8R,9R)-10-Acetyl-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 723413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723413
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:9](=[O:27])[C:8]=3[CH:7]=[CH:6][N:5]2[CH:28]=1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:29]([N:12]1[C:13]2[C:4]3=[N:3][C:2]([CH3:1])=[CH:28][N:5]3[CH:6]=[CH:7][C:8]=2[C:9](=[O:27])[C@H:10]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:23])[CH3:24])[C@H:11]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:31])[CH3:30]

Komponenten

5

Edukt 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 69586205(8R,9R)-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Produkt 1

HCID 69586437(8R,9R)-10-Acetyl-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a of 0° C. cooled solution of 7.00 g (18.5 mmol) (8R,9R)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridin-7-one in toluene (70 ml) is added 4.10 ml (55.5 mmol) acetyl chloride and 7.70 ml (55.5 mmol) triethylamine and the reaction mixture is stirred for 1 h at 0° C. Afterwards further 4.10 ml (55.5 mmol) acetyl chloride and 7.70 ml (55.5 mmol) triethylamine are added to the reaction mixture and it is warmed up to 25° C. and stirred at this temperature for 1 h. Subsequently the reaction is quenched by adding of saturated aqueous ammonium chloride solution. This mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is crystallised from diethyl ether to provide 5.4 g (12.7 mmol/70%) of the title compound as a colourless solid with a melting point of 168–169° C. (diethyl ether).

Aufarbeitung

  1. temperatureis warmed up to 25° C.
  2. stirringstirred at this temperature for 1 h
  3. customSubsequently the reaction is quenched
  4. additionby adding of saturated aqueous ammonium chloride solution
  5. extractionThis mixture is extracted twice with dichloromethane
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried over sodium sulphate
  8. customevaporated in vacuo
  9. customThe crude product is crystallised from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-615587a34ffc43e6a4ab53383756e63a
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141567B2

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