Dimethylamine → 1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-dimethylamino-pent-2-en-1-one

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Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:29]3[C:28]4[CH2:27][CH2:26][N:25]([C:30](=[O:40])[CH:31]=[CH:32][CH2:33][CH2:34]OS(C)(=O)=O)[CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:47][NH:48][CH3:49]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:29]3[C:28]4[CH2:27][CH2:26][N:25]([C:30](=[O:40])[CH:31]=[CH:32][CH2:33][CH2:34][N:48]([CH3:49])[CH3:47])[CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

In a 25 ml rb flask were placed methanesulfonic acid 5-{4-[3-chloro-4-(pyridine-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-oxo-pent-3-enyl ester (0.15 g, 0.25 mmol) in DMF (5.0 ml) and to the solution was added cesium carbonate (0.16 g, 0.5 mmol) followed by dimethylamine (0.5 ml of 2M solution in THF) and heated at 50° C. overnight. The yellow solution was purified by HPLC twice to provide 27.5 mg of light brown solid (20.0%). 1H-NMR (DMSO-d6) δ 8.592-8.574 (m, 1H), 8.378 (s, 1H), 8.181 (s, 1H), 7.890-7.847 (m, 1H), 7.781-7.752 (m, 1H), 7.572-7.552 (d, 1H), 7.514-7.492 (m, 1H), 7.372-7.341 (m, 1H), 7.237-7.207 (m, 1H), 5.271 (s, 2H), 4.942-4.761 (m, 2H), 3.922-3.781 (m, 2H), 3.282-3.169 (m, 4H), 2.343 (m, 2H), 2.127-1.977 (m, 8H). MS m/e 549.1 (M+H), RT=2.26 min

Aufarbeitung

customIn a 25 ml rb flask were placed
customThe yellow solution was purified by HPLC twice

Quellen und Nachweise

ORD-Eintrag: ord-77c8eda28a084b38b14f954214046784
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08501755B2

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