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Nitrogen → N-(3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)oxirane-2-carboxamide

HRID 1482675
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1482675
N#N.CS(O[CH2:8][CH:9]([OH:39])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]2[C:25]([F:26])=[CH:24][N:23]=[C:22]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:30][CH:29]=3)[N:21]=2)[CH:14]=1)=[O:11])(=O)=O.C1COCC1.[H-].[Na+]>C(OCC)(=O)C.O.CCCCCC.C(OCC)(=O)C>[F:26][C:25]1[C:20]([NH:19][C:15]2[CH:14]=[C:13]([NH:12][C:10]([CH:9]3[CH2:8][O:39]3)=[O:11])[CH:18]=[CH:17][CH:16]=2)=[N:21][C:22]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:32][CH:33]=2)=[N:23][CH:24]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 902338843-((3-((5-Fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)amino)-2-hydroxy-3-oxopropyl methanesulfonate

Produkt 1

HCID 89906279N-(3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)oxirane-2-carboxamide
Ausbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a 25 mL 3-neck RBF equipped with N2-bubbler and thermo pocket was charged 3-((3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)amino)-2-hydroxy-3-oxopropyl methanesulfonate (0.03 g) and THF (2.0 mL). The reaction mixture was cooled to 0° C. and NaH (2.2 mg) was added. The reaction mixture was warmed to room temperature and stirred for 45 min. Completion of reaction was monitored on TLC using hexane:ethyl acetate (2:8) as mobile phase. After completion of reaction, the mixture was diluted with ethyl acetate (20 mL) and water was added. The organic layer was dried over sodium sulfate and solvent was removed under reduced pressure. Crude product purified by tituration with diethyl ether to give 0.011 g of N-(3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)oxirane-2-carboxamide. 1H NMR: DMSO-d6 (400 MHz): 2.881 (d, 1H, J=4.4), 2.98 (t, 1H), 3.30 (s, 3H), 3.63 (m, 3H), 4.01 (t, 2H, J=4.0), 6.77 (d, 2H, J=9.2), 7.27 (t, 1H, J=8), 7.35 (d, 1H, J=8.4), 7.52 (d, 3H, J=8.8), 7.93 (s, 1H), 8.07 (d, 1H, J=3.2), 8.99 (s, 1H), 9.37 (d, 1H, J=18), 10.19 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customCompletion of reaction
  3. customAfter completion of reaction
  4. additionwas added
  5. dry with materialThe organic layer was dried over sodium sulfate and solvent
  6. customwas removed under reduced pressure
  7. customCrude product purified by tituration with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-08467d4cc27e402484263c5a8f7ba5bb
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09415049B2

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