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Acetyl chloride → (8R,9R)-8,10-Diacetyl-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 584846
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 584846
[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)[C:9](=[O:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23].[C:24](Cl)(=[O:26])[CH3:25].C(N([CH2:33][CH3:34])CC)C.C(=O)([O-])[OH:36].[Na+]>ClCCl.O>[C:24]([C@@H:10]1[C:9](=[O:21])[C:8]2[CH:7]=[CH:6][N:5]3[C:22]([CH3:23])=[C:2]([CH3:1])[N:3]=[C:4]3[C:13]=2[N:12]([C:33](=[O:36])[CH3:34])[C@H:11]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:26])[CH3:25]
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Komponenten

7

Edukt 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 59943673(8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Produkt 1

HCID 69551346(8R,9R)-8,10-Diacetyl-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

50 g of (8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one (WO 00/17200, example B1) are dissolved under nitrogen and with exclusion of moisture in 450 ml of dichloromethane. Half of the amount of acetyl chloride (46.6 ml in total) is firstly added dropwise at room temperature. Half the amount of triethylamine (45 ml in total) is then added dropwise with ice cooling in the course of 30 min. After stirring at room temperature for 1 h, the procedure is repeated as described with the second half of the reagents indicated. The mixture is then hydrolyzed using saturated sodium hydrogencarbonate solution and water. The organic phase is separated off and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate and evaporated. The yellow-brown residue is coevaporated a further two times with toluene. 64 g of the title compound are isolated as a brown oil, which is used in the next stage without further purification.

Aufarbeitung

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4007de42086140228fe9fbcf0beeda59
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06927292B2

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