2,5-Dimethoxyphenylboronic acid → 4-amino-N-butyl-8-(2,5-dimethoxyphenyl)cinnoline-3-carboxamide

HRID 2375668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375668
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:26]3[CH:27]=[C:22]([O:21][CH3:20])[CH:23]=[CH:24][C:25]=3[O:28][CH3:29])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14]

Komponenten

3

Edukt 2

HCID 27343422,5-Dimethoxyphenylboronic acidHCID 672287024-Amino-8-bromo-N-butyl-cinnoline-3-carboxamide

Produkt 1

HCID 236296614-amino-N-butyl-8-(2,5-dimethoxyphenyl)cinnoline-3-carboxamide

Versuchsvorschrift

The title compound was prepared from 4-amino-8-bromo-N-butyl-cinnoline-3-carboxamide (100 mg, 0.31 mmol) and 2,5-dimethoxyphenyl boronic acid (112.6 mg, 0.62 mmol) according to Method A to afford a white solid (96.3 mg, 82%). 1H NMR (300.132 MHz, CDCl3) δ 8.54 (t, J=4.7 Hz, 1H), 7.86 (dd, J=7.6, 2.2 Hz, 1H), 6.96 (t, J=3.0 Hz, 1H), 6.96 (s, 1H), 6.93 (d, J=1.9 Hz, 1H), 7.76-7.68 (m, 2H), 3.79 (s, 3H), 3.64 (s, 3H), 3.48 (q, J=6.6 Hz, 2H), 1.61 (quintet, J=7.2 Hz, 2H), 1.43 (sextet, J=7.3 Hz, 2H), 0.94 (t, J=7.3 Hz, 3H). MS APCI, m/z=381.2 (M+H). HPLC 2.83 min.

Quellen und Nachweise

ORD-Eintrag
ord-ca0faf087f1243fab453e64353323fce
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465795B2

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