Ethyl 3,3,3-trifluoro-2-oxopropanoate → Tert-butyl 4-(3-oxo-2-(trifluoromethyl)-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)naphthalen-1-ylcarbamate

HRID 217806

Reaktionsgleichung

Reaktionsgleichung von HRID 217806
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[F:28][C:29]([F:38])([F:37])[C:30](=O)[C:31](OCC)=[O:32]>C(O)C>[O:32]=[C:31]1[NH:1][C:2]2[N:3]=[CH:4][CH:5]=[C:6]([O:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[CH:12][CH:11]=3)[C:7]=2[N:8]=[C:30]1[C:29]([F:38])([F:37])[F:28]

Komponenten

4

Edukt 2

HCID 2737239Ethyl 3,3,3-trifluoro-2-oxopropanoateHCID 44186229Tert-butyl 4-(2,3-diaminopyridin-4-yloxy)naphthalen-1-ylcarbamate

Produkt 1

HCID 46900749Tert-butyl 4-(3-oxo-2-(trifluoromethyl)-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)naphthalen-1-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To tert-butyl 4-(2,3-diaminopyridin-4-yloxy)naphthalen-1-ylcarbamate (1.00 g, 2.73 mmol) dissolved in 20 mL of anhydrous ethanol under argon and at reflux was added the ethyl trifluoropyruvate (697 mg, 0.50 mL, 4.10 mmol). The reaction mixture was stirred at reflux for 3 hours. After cooling at RT, a precipitate was formed, filtered off and rinsed with Et2O. tert-butyl 4-(3-oxo-2-(trifluoromethyl)-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)naphthalen-1-ylcarbamate was obtained as a white solid (116 mg, 0.246 mmol, 9%). The filtrate was evaporated under vacuum. The residue was chromatographied (eluent: CH2Cl2/EtOAc: 4/1 towards 0/1) to afford the second isomer as a slightly yellow solid (540 mg, 1.14 mmol, 42%).

Aufarbeitung

  1. temperatureat reflux
  2. temperatureat reflux for 3 hours
  3. customa precipitate was formed
  4. filtrationfiltered off
  5. washrinsed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-2b029e7e085a424c80eec61f20e6ffb3
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198279B2

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