Sodium hydride → N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1-isobutyl-3-methoxy-2-oxo-1,8-naphthyridin-4-yl)acetamide

HRID 13842

Reaktionsgleichung

Reaktionsgleichung von HRID 13842
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:16](=[O:20])[CH2:17][O:18][CH3:19])[C:12]([C:25]#[N:26])=[CH:11][C:10]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1.ClC1C=C(Cl)C=CC=1C1N=C(NCC(C)C)C(C#N)=CC=1C1C=CC(Cl)=CC=1.CO[CH2:64][C:65](Cl)=[O:66].[H-].[Na+].NC1C2C(=NC(C3C=CC(Cl)=CC=3Cl)=C(C3C=CC(Cl)=CC=3)C=2)N(CC(C)C)[C:73](=[O:100])[C:72]=1OC>>[C:73]([N:26]([C:25]1[C:12]2[C:13](=[N:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:10]([C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=3)[CH:11]=2)[N:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:16](=[O:20])[C:17]=1[O:18][CH3:19])[C:65](=[O:66])[CH3:64])(=[O:100])[CH3:72]

Komponenten

6

Edukt 5

HCID 24758Sodium hydrideHCID 96623Methoxyacetyl chlorideHCID 444409945-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(isobutylamino)nicotinonitrileHCID 68716559N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-isobutyl-2-methoxyacetamideHCID 687181664-amino-7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1-isobutyl-3-methoxy-1,8-naphthyridin-2(1H)-one

Produkt 1

HCID 11330739N-acetyl-N-(7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1,2-dihydro-1-isobutyl-3-methoxy-2-oxo-1,8-naphthyridin-4-yl)acetamide

Versuchsvorschrift

N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-isobutyl-2-methoxyacetamide (prepared by the reaction of 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrile with 2-methoxyacetyl chloride using the conditions of EXAMPLE 62 Step A) was reacted with NaH using the conditions of EXAMPLE 80 affording 4-amino-7-(2,4-dichlorophenyl)-6-(4-chlorophenyl)-1-isobutyl-3-methoxy-1,8-naphthyridin-2(1H)-one which was acylated according to the procedure of EXAMPLE 64 affording the title compound. HPLC/MS: 586.0 (M+1), 5587.8 (M+3); Rt =4.64 min.

Quellen und Nachweise

ORD-Eintrag
ord-85aa99d7653f4507b0eccec276bad340
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728141B2

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