3,4-Dimethoxyaniline → 2-(3,4-Dimethoxyphenylamino)-6-(3-acetamidophenyl)pyrazine

HRID 16257

Reaktionsgleichung

Reaktionsgleichung von HRID 16257
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[NH2:23]>>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:23][C:13]2[CH:14]=[N:15][CH:16]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=3)[N:12]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Komponenten

3

Edukt 2

HCID 227703,4-DimethoxyanilineHCID 116874302-(3-Acetamidophenyl)-6-chloropyrazine

Produkt 1

HCID 115886292-(3,4-Dimethoxyphenylamino)-6-(3-acetamidophenyl)pyrazineAusbeute 27,1 %

Versuchsvorschrift

Using Method F with 180 mg (0.73 mmol) 4a and 134 mg (0.88 mmol)3,4-dimethoxyaniline, 72 mg (27.1%) pure title compound were obtained after preparative HPLC (eluent: AcOEt) purification of the whole batch. Reaction time: 6 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 2.07 (s, 3H, CH3CO), 3.73 (s, 3H, CH3O(4)), 3.77 (s, 3H, CH3O(3)), 6.95 (d, 1H, Harom 5, J=8.71), 7.26 (q, 1H, Harom 6, Jo=8.63, Jm=2.35), 7.42 (t, 1H, Harom 5′, J=7.90), 7.62 (s, 1H, Harom 2), 7.64 (d, 1H, Harom 4′ or 6′), 7.72 (d, 1H, Harom 6′ or 4′, J=7.63), 8.13 (s, 1H, HP5), 8.30 (s, 1H, Harom 2′), 8.35 (s, 1H, HP3), 9.45 (s, 1H, NHamino), 10.07 (s, 1H, NHamido); MS, (C20H20N4O3), m/z: 365.3 [M++1, 100].

Quellen und Nachweise

ORD-Eintrag
ord-00593f974dad40939c65dd9dd5a161ac
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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