4-Chlorobenzoyl chloride → 2-(3,4,5-Trimethoxyphenylamino)-6-[4-(4-chlorophenylcarbonyl)-aminophenyl]-pyrazine

HRID 16317

Reaktionsgleichung

Reaktionsgleichung von HRID 16317
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16](OC3C=CC(N)=CC=3)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](Cl)=[O:36])=[CH:31][CH:30]=1>CCOC(C)=O>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16]([C:4]3[CH:3]=[CH:8][C:7]([C:35]([C:32]4[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=4)=[O:36])=[CH:6][C:5]=3[NH2:13])[N:15]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Komponenten

4

Edukt 2

HCID 85014-Chlorobenzoyl chlorideHCID 593434392-(3,4,5-Trimethoxyphenylamino)-6-(4-aminophenyloxy)-pyrazine

Produkt 1

HCID 669125052-(3,4,5-Trimethoxyphenylamino)-6-[4-(4-chlorophenylcarbonyl)-aminophenyl]-pyrazineAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Using Method LL with 2-(3,4,5-trimethoxyphenylamino)-6-(4-aminophenyloxy)-pyrazine (50 mg, 0.14 mmol) and 4-chlorophenylcarbonyl chloride (22 μL, 0.17 mmol), and purification by column chromatography (AcOEt), the title compound was obtained (23 mg). Yield: 34%. 1H NMR (250 MHz, DMSO-d6) δ 3.65 (s, 3H, [CH3O]4), 3.85 (s, 6H, [CH3O]3+5), 7.28 (s, 2H, Harom2′+6′), 7.64 (d, 2H, Harom 3+5, J=8.5 Hz), 7.93 (d, 2H, Harom 3″+5″, J=8.6 Hz), 7.93 (m, 2H, Harom 2″+6″), 8.03 (m, 2H, Harom 2+6), 8.14 (s, 1H, HPz 5), 8.53 (s, 1H, HPz 3), 9.56 (s, 1H, NH), 10.50 (s, 1H, NHamide). m/z 491.1 [(M+H)+ calcd for C26H23ClN4O4 490.1].

Quellen und Nachweise

ORD-Eintrag
ord-e19b706740cc476bb169dce6fb387e94
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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