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Sodium methanethiolate → 3,4-Dichloro-5-methyl-N-{1-[2-(methylthio)pyrimidin-4-yl]piperidin-4-yl}-1H-pyrrole-2-carboxamide

HRID 2234040
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2234040
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH2:14][CH2:13]1)=[O:10].[CH3:25][S-:26].[Na+]>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:26][CH3:25])[N:19]=2)[CH2:14][CH2:13]1)=[O:10]
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Komponenten

6

Edukt 2

HCID 4378561Sodium methanethiolateHCID 866083433,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

Produkt 1

HCID 685798923,4-Dichloro-5-methyl-N-{1-[2-(methylthio)pyrimidin-4-yl]piperidin-4-yl}-1H-pyrrole-2-carboxamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 307, 200 mg, 0.515 mmol) and sodium thiomethoxide (108.2 mg, 1.545 mmol) were combined in DMF (12 ml) and heated at 90° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with EtOAc and water. The phases were separated, and the aqueous phase was extracted three times with EtOAc. The combined organic portions were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a peach coloured solid (200 mg, 0.499 mmol, 97% yield) that was used without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted three times with EtOAc
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1ef28c3748404045a8c39f011a2461df
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709503B2

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