Trifluoroacetic acid → HCID 68325413, Verbindung

HRID 2403304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2403304
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][N:22]=3)=[C:16]([F:30])[CH:15]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O>C(#N)C.O>[CH2:28]([O:27][C:24]1[CH:23]=[N:22][C:21]([NH:20][C:17]2[CH:18]=[CH:19][C:14]([CH:10]3[O:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:15][C:16]=2[F:30])=[N:26][CH:25]=1)[CH3:29]

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 68325477HCID 68325477, Verbindung

Produkt 1

HCID 68325413HCID 68325413, VerbindungAusbeute 109,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of (RS)-2-[4-(5-ethoxy-pyrimidin-2-ylamino)-3-fluoro-phenyl]-morpholine-4-carboxylic acid tert-butyl ester (12 mg) in acetonitrile (1.5 ml) and water (3 ml) was added trifluoroacetic acid (22.0 μl). The reaction mixture was then capped and the mixture was shaken at 80° C. for 3.5 h. The reaction mixture was then cooled to room temperature and poured into EtOAc and washed with 1 M aq. NaOH. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH) to afford (RS)-(5-ethoxy-pyrimidin-2-yl)-(2-fluoro-4-morpholin-2-yl-phenyl)-amine (10 mg, quant.) as an off-white solid. MS (ISP): 319.2 ([ M+H]+).

Aufarbeitung

  1. customThe reaction mixture was then capped
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washwashed with 1 M aq. NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-20e75ec08fe243eea03ff6635fba3b15
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802673B2

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