Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Reserpine | HCID 5770 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Edukt | N5,N5-Dimethylpyridine-2,5-diamine | HCID 5743468 | — |
| Edukt | 2-[4-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl]acetic acid | HCID 66906632 | — |
| Edukt | HCID 178526252 | HCID 178526252 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 11719537 | HCID 11719537 | 73,1% |
Reaktionsschritte
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.101 g) and 2-hydroxypyridine N-oxide (0.059 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetic acid (0.15 g), 2-amino-5-dimethylaminopyridine (0.073 g), diisopropylethylamine (0.092 ml) and DMF (2 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The resultant reaction mixture was transferred onto a Waters ‘β Basic Hypersil’ reversed-phase preparative HPLC column (5 microns silica, 30 mm diameter, 250 mm length) that was eluted with decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.148 g); 1H NMR: (DMSOd6) 2.88 (s, 6H), 3.71 (s, 2H), 3.98 (s, 3H), 3.98 (s, 3H), 7.19 (m, 1H), 7.25 (d, 2H), 7.38 (s, 1H), 7.44 (d, 2H), 7.55 (s, 1H), 7.84 (d, 1H), 7.90 (d, 1H), 8.53 (s, 1H), 10.43 (s, 1H); Mass Spectrum: M+H+ 460.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US08153643B2 |
|---|
| Quelldatensatz | uspto-grants-2012_04 |
|---|
| ORD ID | ord-d3d4abec0e974059a69ce6da66cdfd06 |
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| Quellennotiz | uspto-grants-2012_04 |
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