N,N-Diisopropylmethylamine → 4-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)C)(C)C.[CH3:28][O:29][CH2:30]/[CH:31]=[CH:32]/[C:33](Cl)=[O:34].C(=O)(O)[O-].[Na+].[Cl-].[Na+].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:33](=[O:34])[CH:32]=[CH:31][CH2:30][O:29][CH3:28])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of 1.0 g of N-(3-bromophenyl)-4,6-quinazolindiamine and 0.62 g of diisopropyl methylamine in 21 mL of tetrahydrofuran at 0° C. was added 0.62 g of 4-methoxycrotonyl chloride. The mixture was stirred at 0° C. for 1.5 hr and 10 min at room temperature. The mixture was poured into saturated sodium bicarbonate-brine and extracted with ethyl acetate. The organic solution was dried over magnesium sulfate. The solution was filtered through silica gel and the solvent was removed. The residue was recrystallized from 1-butanol to give 1.25 g of 4-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide as a yellow solid: mass spectrum (m/e): M+H 415.0.
Aufarbeitung
- extractionextracted with ethyl acetate
- dry with materialThe organic solution was dried over magnesium sulfate
- filtrationThe solution was filtered through silica gel
- customthe solvent was removed
- customThe residue was recrystallized from 1-butanol
Quellen und Nachweise
- ORD-Eintrag
- ord-140e71bc53c54d56aec6bd1923a12126
- Quelldatensatz
- uspto-grants-2001_06
- Patentnummer
- US06251912B1
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