Acetoxyacetyl chloride → 2-{[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]amino}-2-oxoethyl acetate

HRID 13818

Reaktionsgleichung

[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].[C:32]([O:35][CH2:36][C:37](Cl)=[O:38])(=[O:34])[CH3:33]>C(#N)C.CCOC(C)=O>[C:32]([O:35][CH2:36][C:37]([NH:14][C:13]1[C:12]2[C:7](=[N:8][C:9]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[C:10]([C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[CH:11]=2)[N:6]([CH3:30])[C:5](=[O:31])[C:4]=1[C:1](=[O:3])[CH3:2])=[O:38])(=[O:34])[CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To the product of Example 2 (120 mg) in acetonitrile (2 mL) was added acetoxyacetyl chloride (0.2 mL). The reaction was heated to 90° C. in a CEM microwave reactor for a total of 34 minutes. The reaction was diluted with EtOAc and was washed with saturated aqueous NaHCO3 solution. The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-60% EtOAc in hexane affording the title compound. HPLC/MS: 572.1 (M+1), 574.1 (M+3); Rt=4.06 min.

Aufarbeitung

washwas washed with saturated aqueous NaHCO3 solution
customThe concentrated residue was purified by flash chromatography on silica gel gradient
washeluted with 0-60% EtOAc in hexane affording the title compound

Quellen und Nachweise

ORD-Eintrag: ord-6bbe050a73ec42f596a556812d626ba7
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07728141B2

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