Sodium Methoxide → HCID 11620207, Verbindung

HRID 1042646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042646
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13](F)=[C:14]([CH:34]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:16])=[CH:4][N:3]=1.[CH3:36][O-:37].[Na+]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([O:37][CH3:36])=[C:14]([CH:34]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:16])=[CH:4][N:3]=1

Komponenten

3

Edukt 2

HCID 10942334Sodium MethoxideHCID 16109018HCID 16109018, Verbindung

Produkt 1

HCID 11620207HCID 11620207, Verbindung

Versuchsvorschrift

A mixture of 5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluoro-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide (0.14 g, 0.29 mmol) and NaOMe (0.5 M solution in methanol, 2.0 mL, 1.0 mmol) in a sealed tube was heated to reflux. After 16 h, the reaction was cooled and partitioned between EtOAc and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The material was purified by preparative TLC, eluting with 30% acetone/dichloromethane to give 5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-methoxy-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide as a white solid. MS m/z=496 [M+H]+. Calc'd for C26H24F3N5O2: 495.

Aufarbeitung

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was cooled
  3. custompartitioned between EtOAc and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by preparative TLC
  8. washeluting with 30% acetone/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-9d384534050642f5a3bb2b48f9de4ce6
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557996B2

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