Diisopropylethylamine → N-(3-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenyl)-3-(trifluoro-methoxy)benzamide

HRID 217861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217861
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][C:6]1[C:15]2[N:14]=[CH:13][C:12](=[O:16])[NH:11][C:10]=2[N:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.[F:29][C:30]([F:42])([F:41])[O:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36]>C1COCC1>[O:16]=[C:12]1[NH:11][C:10]2[N:9]=[CH:8][CH:7]=[C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][CH:40]=[C:32]([O:31][C:30]([F:29])([F:41])[F:42])[CH:33]=4)[CH:19]=[CH:18][CH:17]=3)[C:15]=2[N:14]=[CH:13]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5228543-(Trifluoromethoxy)benzoyl chlorideHCID 469015938-(3-aminophenoxy)pyrido[2,3-b]pyrazin-3(4H)-one

Produkt 1

HCID 44133722N-(3-(3-oxo-3,4-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenyl)-3-(trifluoro-methoxy)benzamideAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Method G1: 8-(3-aminophenoxy)pyrido[2,3-b]pyrazin-3(4H)-one (43 mg, 0.169 mmol) and diisopropylethylamine (44 μL, 0.254 mmol) were mixed in dry THF (5.0 mL) and 3-trifluoromethoxybenzoyl chloride (57 mg, 0.254 mmol) was added. This mixture was heated to reflux for 17 h. After cooling at RT, the solvent was removed in vacuo. The obtained oily residue was dissolved in DCM and washed with water and dried over MgSO4. After evaporation of DCM, the residue was retaken in Et2O, triturated and filtered off to afford the title compound as a white solid (45 mg, 60%).

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 17 h
  3. customthe solvent was removed in vacuo
  4. dissolutionThe obtained oily residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customAfter evaporation of DCM
  8. customtriturated
  9. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-d4fe96ef61654d3683de6317cda2ca69
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198279B2

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