Methyl iodide → N-[3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N-methylacetamide

HRID 13810

Reaktionsgleichung

Reaktionsgleichung von HRID 13810
[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][C:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2].IC.[C:34]([O-])([O-])=O.[Cs+].[Cs+].C1C[O:43][CH2:42][CH2:41]1>>[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[N:14]([CH3:34])[C:42](=[O:43])[CH3:41])=[CH:11][C:10]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 112600073-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Produkt 1

HCID 11341526N-[3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N-methylacetamide

Versuchsvorschrift

A solution of the product from Example 2 (60 mg) in THF (1 mL), under nitrogen, was treated with iodomethane (73 uL) and Cs2CO3 (58 mg). The suspension was stirred overnight. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification on a preparative silica TLC plate eluted with 25% EtOAc in hexane afforded the title compound. HPLC/MS: 528.1 (M+1), 530.1 (M+3); Rt=4.08 min.

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification on a preparative silica TLC plate
  7. washeluted with 25% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-5eb9e7fa91e14297917b7a7df98dfbc3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728141B2

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