1,3-Benzodioxol-5-amine → 2-(3,4-Methylenedioxyphenylamino)-6-(3-acetamidophenyl)pyrazine

HRID 16258

Reaktionsgleichung

Reaktionsgleichung von HRID 16258
[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].[CH2:18]1[O:27][C:26]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=2[O:19]1>>[CH2:18]1[O:27][C:26]2[CH:25]=[CH:24][C:22]([NH:23][C:13]3[CH:14]=[N:15][CH:16]=[C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=4)[N:12]=3)=[CH:21][C:20]=2[O:19]1

Komponenten

3

Edukt 2

HCID 843101,3-Benzodioxol-5-amineHCID 116874302-(3-Acetamidophenyl)-6-chloropyrazine

Produkt 1

HCID 115011422-(3,4-Methylenedioxyphenylamino)-6-(3-acetamidophenyl)pyrazineAusbeute 73,1 %

Versuchsvorschrift

Using Method F with 200 mg (0.33 mmol) 4a and 138 mg (1.0 mmol) 3,4-methylendioxyaniline, 84 mg (29.0%) pure title compound were obtained after preparative HPLC (eluent: AcOEt) purification of the whole batch. Reaction time: 18 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 2.08 (s, 3H, CH3CO), 5.99 (s, 2H, OCH2O), 6.91 (d, 1H, Harom 5, J=8.40), 7.32 (q, 1H, Harom 6, Jo=8.43, Jm=1.99), 7.40 (d, 1H, Harom 2, J=1.85), 7.43 (t, 1H, Harom 5′, J=7.87), 7.65 (d, 1H, Harom 4′ or 6′, J=8.93), 7.68 (d, 1H, Harom 6′ or 4′, J=7.83), 8.12 (s, 1H, HP5), 8.30 (s, 1H, Harom 2′), 8.35 (s, 1H, HP3), 9.42 (s, 1H, NHamino), 10.09 (s, 1H, NHamido); MS, (C19H16N4O3), m/z: 349.1 [M++1, 100].

Quellen und Nachweise

ORD-Eintrag
ord-3612e6fa08334b608f82e6cc4d9e46f1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

Verknüpfte Notizen

Wird geladen…