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Potassium Carbonate → 4-(3-(1-(7-Chloroquinazolin-2-YL)azetidin-3-YL)pyrazin-2-YL)-2-fluoro-N-methylbenzamide

HRID 2364586
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2364586
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH:22]1[CH2:25][CH:24]([C:26]2[C:27]([C:32]3[CH:41]=[CH:40][C:35]([C:36]([NH:38][CH3:39])=[O:37])=[C:34]([F:42])[CH:33]=3)=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:23]1.Cl[C:44]1[N:53]=[CH:52][C:51]2[C:46](=[CH:47][C:48]([Cl:54])=[CH:49][CH:50]=2)[N:45]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.O>[Cl:54][C:48]1[CH:47]=[C:46]2[C:51]([CH:52]=[N:53][C:44]([N:22]3[CH2:23][CH:24]([C:26]4[C:27]([C:32]5[CH:41]=[CH:40][C:35]([C:36]([NH:38][CH3:39])=[O:37])=[C:34]([F:42])[CH:33]=5)=[N:28][CH:29]=[CH:30][N:31]=4)[CH2:25]3)=[N:45]2)=[CH:50][CH:49]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 124139292,7-DichloroquinazolineHCID 867054064-(3-(Azetidin-3-YL)pyrazin-2-YL)-2-fluoro-N-methylbenzamide tris(2,2,2-trifluoroacetate)

Produkt 1

HCID 727148524-(3-(1-(7-Chloroquinazolin-2-YL)azetidin-3-YL)pyrazin-2-YL)-2-fluoro-N-methylbenzamideAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 263
1-Butanol
Lösungsmittel
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

4-(3-(Azetidin-3-yl)pyrazin-2-yl)-2-fluoro-N-methylbenzamide tris(2,2,2-trifluoroacetate) (0.150 g, 0.239 mmol), 2,7-dichloroquinazoline (0.062 g, 0.310 mmol), and potassium carbonate (0.165 g, 1.19 mmol, Aldrich) were mixed in butan-1-ol (2 mL) in a sealed tube. The reaction mixture was stirred at 110° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was separated, washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude mixture was purified via silica gel flash column chromatography eluting with 50% to 100% EtOAc in hexanes to yield give 99 mg (92%) of a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.09 (d, J=4.50 Hz, 3H) 4.29-4.38 (m, 1H) 4.46-4.58 (m, 4H) 6.75-6.85 (br. m., 1H) 7.18 (dd, J=8.61, 1.56 Hz, 1H) 7.36 (d, J=12.32 Hz, 1H) 7.40 (dd, J=8.12, 1.27 Hz, 1H) 7.60 (d, J=8.41 Hz, 1H) 7.63 (br. s., 1H) 8.27 (t, J=8.02 Hz, 1H) 8.57 (d, J=2.15 Hz, 1H) 8.65 (d, J=2.15 Hz, 1H) 8.97 (s, 1H). m/z=449 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude mixture was purified via silica gel flash column chromatography
  9. washeluting with 50% to 100% EtOAc in hexanes
  10. customto yield

Quellen und Nachweise

ORD-Eintrag
ord-15ec5f4236be4e14a60f6317108ee5ec
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691986B2

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