2,4-Dimethoxypyrimidine-5-boronic acid pinacol ester → 4-amino-N-butyl-8-(2,4-dimethoxypyrimidin-5-yl)cinnoline-3-carboxamide

HRID 2375671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375671
[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[N:27]=[C:26]([O:28][CH3:29])[C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][N:23]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:25]3[C:26]([O:28][CH3:29])=[N:27][C:22]([O:21][CH3:20])=[N:23][CH:24]=3)[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 162183882,4-Dimethoxypyrimidine-5-boronic acid pinacol esterHCID 672287024-Amino-8-bromo-N-butyl-cinnoline-3-carboxamide

Produkt 1

HCID 251334414-amino-N-butyl-8-(2,4-dimethoxypyrimidin-5-yl)cinnoline-3-carboxamide

Versuchsvorschrift

The title compound was prepared from 4-amino-8-bromo-N-butyl-cinnoline-3-carboxamide (200.0 mg, 0.62 mmol) and 2,4-dimethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine (987.9 mg, 3.72 mmol) according to Method B to afford a white solid (162.1 mg, 69%). 1H NMR (300.132 MHz, CDCl3) δ 8.49 (t, J=5.5 Hz, 1H), 8.33 (s, 1H), 7.90 (dd, J=7.6, 2.1 Hz, 1H), 7.77-7.69 (m, 3H), 4.07 (s, 3H), 3.93 (s, 3H), 3.50 (q, J=6.6 Hz, 2H), 1.63 (quintet, J=7.2 Hz, 2H), 1.44 (sextet, J=7.4 Hz, 2H), 0.95 (t, J=7.3 Hz, 3H). MS APCI, m/z=383.1 (M+H). HPLC 2.52 min.

Quellen und Nachweise

ORD-Eintrag
ord-567659ce0b954b519c646e0ed1d4d49e
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465795B2

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