Diisopropylethylamine → 1-[4-(4-Fluoro-2-trifluoromethyl-benzoyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yloxy]-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029182
[O:1]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16](=[O:22])[NH:17]4)[CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[C:30]([C:37]([F:40])([F:39])[F:38])[CH:29]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([N:4]2[C:5]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:21]=[CH:20][N:19]=[C:18]5[C:13]=4[C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16](=[O:22])[NH:17]5)=[CH:7][C:6]=3[O:1][CH2:2][CH2:3]2)=[O:33])=[C:30]([C:37]([F:38])([F:39])[F:40])[CH:29]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 698108831-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yloxy)-5H-benzo[c][1,8]naphthyridin-6-one

Produkt 1

HCID 581683171-[4-(4-Fluoro-2-trifluoromethyl-benzoyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yloxy]-5H-benzo[c][1,8]naphthyridin-6-oneAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Compound 218 (50 mg, 0.14 mmol), 4-fluoro-2-trifluoromethyl-benzoyl chloride (49 mg, 0.22 mmol), and DIEA (0.07 mL, 0.43 mmol) were dissolved in dioxane (2 mL) and stirred for 1 h at room temperature. The reaction was quenched with H2O, diluted with EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 100% EtOAc in hexanes to provide 219 (28 mg, 36% yield) as a tan solid. LC-MS (M+H=536, obsd.=536).

Aufarbeitung

  1. customThe reaction was quenched with H2O
  2. additiondiluted with EtOAc
  3. filtrationfiltered through an Extrelut column
  4. washThe column was washed with EtOAc
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified via Biotage
  7. washeluting with a gradient of 0 to 100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-311809829cac4e0fbf0367e19400e909
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735584B2

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